3-(Triphenyl-lambda~5~-phosphanylidene)butan-2-one → 1-Allyloxycarbonyl-3-(2-methyl-3-oxo-1-butenyl)pyrrolidine

HRID 1090519Notes

Reaction equation

HRID 1090519 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8]1)=[O:6])[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:21]([CH3:25])[C:22](=[O:24])[CH3:23])C=CC=CC=1>ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][CH:9]([CH:12]=[C:21]([CH3:25])[C:22](=[O:24])[CH3:23])[CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 3019223-(Triphenyl-lambda~5~-phosphanylidene)butan-2-oneHCID 199148771-Allyloxycarbonyl-3-formylpyrrolidine

Product 1

HCID 572093001-Allyloxycarbonyl-3-(2-methyl-3-oxo-1-butenyl)pyrrolidineYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-allyloxycarbonyl-3-formylpyrrolidine (13.45 g) and 3-triphenylphosphoranylidenebutan-2-one (25.60 g) in dichloromethane (15 ml) was refluxed for 20 hours. The mixture was concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (200 g) and eluted with a mixture of ethyl acetate and hexane (4:6 V/V) to give 1-allyloxycarbonyl-3-(2-methyl-3-oxo-1-butenyl)pyrrolidine (16.52 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a syrup
  3. washeluted with a mixture of ethyl acetate and hexane (4:6 V/V)

Sources & evidence

ORD record
ord-f432b0c1bb774f1b9a2b3e05eb8c8a6b
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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