Methyl trifluoromethyl ketone → Benzyl 4,4,4-trifluoro-3-methylbut-2-enoate

HRID 216352Notes

Reaction equation

HRID 216352 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([CH3:5])=O.C1(P(=[CH:27][C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([CH3:5])=[CH:27][C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29]

Participants

4

Reactant 2

HCID 9871Methyl trifluoromethyl ketoneHCID 3862746Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetate

Product 1

HCID 66705445Benzyl 4,4,4-trifluoro-3-methylbut-2-enoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,1-Trifluoroacetone (680 mg, 6.1 mmol) was added to an ambient temperature solution of benzyl (triphenylphosphoranylidene)acetate (2.5 g, 6.1 mmol) in methylene chloride (10 mL). After stirring in a sealed tube for 72 h, the reaction mixture was concentrated in vacuo. Chromatography over silica eluting with 0-20% ethyl acetate/hexane afforded benzyl 4,4,4-trifluoro-3-methylbut-2-enoate.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-787f6bbc5f2b4757878113bd726cbc64
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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