Benzaldehyde → trans-4-Methoxycarbonyl-5-phenyl-2-oxazoline

HRID 653824Notes

Reaction equation

HRID 653824 reaction equation
C[CH:2]([N+:7]#[C-:8])[C:3]([O:5][CH3:6])=[O:4].[CH:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH3:6][O:5][C:3]([C@H:2]1[C@H:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:16][CH:8]=[N:7]1)=[O:4]

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 2734780Methyl 2-isocyanopropanoate

Product 1

HCID 11195076trans-4-Methoxycarbonyl-5-phenyl-2-oxazolineYield 90%

Procedure

Methyl α-methylisocyano-acetate was reacted with benzaldehyde in the presence of the same catalyst and under the same reaction conditions of those of Example 2. After the solvent was concentrated, the reaction mixture was subjected to silica-gel column chromatography to obtain trans-4-methoxycarbonyl-5- phenyl-2-oxazoline and the corresponding cis-form in a ratio of 87/13). Total yield: 90%. The optical purity of the trans-(4S,5R) form was measured in the same manner as in Example 1, which was 93% ee.

Workup

  1. concentrationAfter the solvent was concentrated

Sources & evidence

ORD record
ord-5929a11caa0044a7b0ce4f88af819ad6
Source dataset
uspto-grants-1992_07
Patent number
US05128478

Reaction notes

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