trans-Crotonyl chloride → (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one

Reaction equation

[C:1](Cl)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[C:7]1([C@@H:13]2[CH2:17][O:16][C:15](=[O:18])[NH:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[CH3:4]/[CH:3]=[CH:2]/[C:1]([N:14]1[C@H:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:17][O:16][C:15]1=[O:18])=[O:5]

Participants

Reactant 2

HCID 643131trans-Crotonyl chloride

HCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-one

Product 1

HCID 10242987(R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-oneYield 81.1%

Procedure

trans-Crotonoyl chloride (2.67 g, 10.24 mmol, Aldrich) was coupled with (R)-4-phenyl-2-oxazolidinone (1.46 g, 8.9 mmol) according to the procedure of Example 1c to afford the title compound (1.67 g). MS m/z 232 (M+H)+, 249 (M+NH4)+.

Sources & evidence

ORD record: ord-2b7ae0440cbb449b91c594c90e18c87f
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618949

Reaction notes

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