Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (S,E)-tert-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 2104372

Reaction equation

HRID 2104372 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]=O)[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([CH:22]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH2:20][CH3:21])=[O:18]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[CH:22]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-

Product 1

HCID 10732902(S,E)-tert-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylateYield 111.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture comprising (4R)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylic acid tert-butyl ester (11.7 g), (carbethoxymethylene)triphenylphosphorane (20.7 g), and toluene (100 mL) was stirred at 100° C. for 18 hours. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1), to thereby give the title compound (17 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-896b2569bd9144c4a0f614a97fcaf480
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Linked notes

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