Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 1283719-20-9

HRID 1496937Notes

Reaction equation

HRID 1496937 reaction equation
[F:1][C:2]1([F:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[C:10]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:12][CH2:13][CH3:14])=[O:11]>C1COCC1>[F:1][C:2]1([F:9])[CH2:7][CH2:6][C:5](=[CH:15][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 157890924,4-Difluorocyclohexanone

Product 1

HCID 1177620081283719-20-9Yield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,4-difluorocyclohexan-1-one (1.0 g, 7.46 mmol, 1.00 equiv) and (carbethoxymethylene)triphenylphosphorane (3.9 g, 24.05 mmol, 1.50 equiv) in THF (20 mL) was stirred under argon overnight at 65° C. After cooling to ambient temperature, the mixture was concentrated under reduced pressure and the crude residue was purified using flash column chromatography (silica gel, EtOAc/petroleum ether (1:10)) to yield 1.5 g (97%) of a colorless oil. 1H-NMR (400 MHz, CDCl3): δ ppm 5.75 (s, 1H), 4.18 (m, 2H), 3.06 (t, J=6.8 Hz, 2H), 2.34 (t, J=6.8 Hz, 2H), 2.11-1.99 (m, 4H), 1.33-1.26 (m, 3H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe crude residue was purified

Sources & evidence

ORD record
ord-120e2cfa24944ec98dc989dfe483b914
Source dataset
uspto-grants-2015_12
Patent number
US09199945B2

Reaction notes

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