Standard Article

2-[(4R)-4,5-Dihydro-4-phenyl-2-oxazolyl]-6-methylpyridine

  1. Giorgio Chelucci

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01625

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Chelucci, G. 2013. 2-[(4R)-4,5-Dihydro-4-phenyl-2-oxazolyl]-6-methylpyridine. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. Università di Sassari, Sassari, Italy

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

(used as a ligand in asymmetric catalytic reactions)

Physical Data: clear pale yellow oil; inline image +77.5° (c 1.61, CHCl3); 1H NMR (400 Mz, CDCl3) δ 7.99 (d, 1H, J = 8.0 Hz), 7.67 (t, 1H, J = 8.0 Hz), 7.38–7.25 (m, 7H), 5,44 (dd, 1H, J = 12.0, 8.0 Hz), 4.89 (dd, 1H, J = 12.0, 8.0 Hz), 4.38 (t, 1H, J = 8.0 Hz), 2.66 (s, 3H); 13C NMR (100.6 Mz, CDCl3) δ 163.9, 158.7, 145.9. 141.8, 136.7, 128.6, 127.5, 126.7, 125.4, 121.3, 75.2, 70.1, 24.5; HRMS: m/z (ESI) calculated [M+H]+ = 257.1285, measured 257.1273 (Δ = 4.7 ppm); elemental analysis calculated for C15H14N2O2: C, 75.61; H, 5.92; N, 11.76; found C, 75.83; H, 5.94; N, 11.72.

Solubility: soluble in most organic solvents (Et2O, CH2Cl2, CHCl3, MeOH, etc.).

Form Supplied in: not commercially available.

Handling, Storage, and Precautions: store in the dark under inert atmosphere.

Preparative Methods: the title compound is prepared by heating under reflux a solution of 6-methylpyridine-2-carbonitrile and (R)-phenylglycinol in the presence of a catalytic amount of zinc chloride in chlorobenzene (eq 1).1, 2 Alternatively, the S enantiomer of the title compound is prepared in a two-step procedure. 6-Methylpyridine-2-carboxylic acid is reacted with isobutyl chloroformate and (S)-phenyl glycinol to afford the related amide, followed by treatment with p-toluenesulfonyl chloride to furnish the target product (eq 2).3

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original image(2)

Featured Compounds

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  1. 1 - 34
Compound Information
Molecular Weight:118.1359
Molecular Formula:C7H6N2
InChIKey:CMADFEQMYFNYCF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:IJXJGQCXFSSHNL-QMMMGPOBSA-N
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Compound Information
Molecular Weight:238.2845
Molecular Formula:C15H14N2O
InChIKey:ZBYAUOZWGYIGNW-AWEZNQCLSA-N
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Compound Information
Molecular Weight:136.315
Molecular Formula:Cl2Zn
InChIKey:Not Available
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Compound Information
Molecular Weight:112.557
Molecular Formula:C6H5Cl
InChIKey:MVPPADPHJFYWMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:LTUUGSGSUZRPRV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:IJXJGQCXFSSHNL-MRVPVSSYSA-N
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Compound Information
Molecular Weight:256.2997
Molecular Formula:C15H16N2O2
InChIKey:ZOAGOUIAGCGLDK-CQSZACIVSA-N
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Compound Information
Molecular Weight:101.1469
Molecular Formula:C5H11NO
InChIKey:SJRJJKPEHAURKC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.577
Molecular Formula:C5H9ClO2
InChIKey:YOETUEMZNOLGDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:238.2845
Molecular Formula:C15H14N2O
InChIKey:ZBYAUOZWGYIGNW-CQSZACIVSA-N
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Compound Information
Molecular Weight:190.647
Molecular Formula:C7H7ClO2S
InChIKey:YYROPELSRYBVMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:122.1677
Molecular Formula:C7H10N2
InChIKey:VHYFNPMBLIVWCW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.959
Molecular Formula:C2H4Cl2
InChIKey:WSLDOOZREJYCGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.3077
Molecular Formula:C17H16O2
InChIKey:UVJZGFKZGQSKDV-OUKQBFOZSA-N
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Compound Information
Molecular Weight:132.1146
Molecular Formula:C5H8O4
InChIKey:BEPAFCGSDWSTEL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:324.3704
Molecular Formula:C20H20O4
InChIKey:RTUIHIVPYZLWPB-CLVCIHKQSA-N
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Compound Information
Molecular Weight:324.3704
Molecular Formula:C20H20O4
InChIKey:RTUIHIVPYZLWPB-TUQDCPSNSA-N
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Compound Information
Molecular Weight:365.89
Molecular Formula:C6H10Cl2Pd2
InChIKey:OTBRMLNJALKXGN-UHFFFAOYSA-L
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Compound Information
Molecular Weight:203.4294
Molecular Formula:C8H21NOSi2
InChIKey:SIOVKLKJSOKLIF-CMDGGOBGSA-N
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Compound Information
Molecular Weight:98.1423
Molecular Formula:C2H3KO2
InChIKey:Not Available
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Compound Information
Molecular Weight:104.1491
Molecular Formula:C8H8
InChIKey:PPBRXRYQALVLMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1026
Molecular Formula:C4H6N2O2
InChIKey:Not Available
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:SRGUIJLJERBBCM-WDEREUQCSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:SRGUIJLJERBBCM-MNOVXSKESA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:SRGUIJLJERBBCM-QWRGUYRKSA-N
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Compound Information
Molecular Weight:190.2384
Molecular Formula:C12H14O2
InChIKey:SRGUIJLJERBBCM-GHMZBOCLSA-N
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Compound Information
Molecular Weight:212.615
Molecular Formula:CHCuF3O3S
InChIKey:YNYHGRUPNQLZHB-UHFFFAOYSA-M
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:332.45
Molecular Formula:C4F6O4Pd
InChIKey:PBDBXAQKXCXZCJ-UHFFFAOYSA-L
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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