Triphenylphosphine → 3-Oxo-cyclopentanecarboxylic acid methyl ester

HRID 1265173

Reaction equation

HRID 1265173 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 2376403-Oxo-cyclopentanecarboxylic acid methyl esterYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-614990dbe74b4f5a94ab46b9806897b9
Source dataset
uspto-grants-2003_04
Patent number
US06545023B2

Linked notes

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