Triphenylphosphine → 3-Oxo-cyclopentanecarboxylic acid methyl ester

HRID 1265173

반응식

HRID 1265173 반응식
C=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1.[O:11]=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[O:11]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 24823OzoneHCID 557110Methyl 3-methylidenecyclopentane-1-carboxylate

생성물 1

HCID 2376403-Oxo-cyclopentanecarboxylic acid methyl ester수율 54%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of methyl 3-methylenecyclopentane carboxylate (Trost, B. M., Chan, M. T., J. Am. Chem. Soc., 1983, 105, 2315) (2.84 g, 20.26 mmol) in dichloromethane (60 mL) was cooled to −78° C. and a slow stream of ozone was passed through until the permanent blue color indicated complete ozonide formation. The excess ozone was purged with stream of nitrogen. Triphenylphosphine (10.62 g, 40.52 mmol) was added, and stirring was continued overnight, allowing the temperature to warm up to ambient. Solvent was removed in vacuo, the residue dissolved in 10 mL of ethyl acetate/hexane (1:4) mixture. The crystalline triphenylphosphine oxide was removed by filtration, and the residue was purified by mplc (ethyl acetate/hexanes (1:4) to yield 1.5651 g (54%) of the desired product.

후처리

  1. customThe excess ozone was purged with stream of nitrogen
  2. temperatureto warm up to ambient
  3. customSolvent was removed in vacuo
  4. dissolutionthe residue dissolved in 10 mL of ethyl acetate/hexane (1:4) mixture
  5. customThe crystalline triphenylphosphine oxide was removed by filtration
  6. customthe residue was purified by mplc (ethyl acetate/hexanes (1:4)

출처 및 근거

ORD 기록
ord-614990dbe74b4f5a94ab46b9806897b9
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06545023B2

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