Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 3-(4,4-difluorocyclohexyl)prop-2-enoate

HRID 2178504Notes

Reaction equation

HRID 2178504 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:25][C:26]1([F:34])[CH2:31][CH2:30][CH:29]([CH:32]=O)[CH2:28][CH2:27]1>C1COCC1>[F:25][C:26]1([F:34])[CH2:31][CH2:30][CH:29]([CH:32]=[CH:4][C:3]([O:2][CH3:1])=[O:24])[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 113555624,4-Difluorocyclohexane-1-carbaldehyde

Product 1

HCID 123135798Methyl 3-(4,4-difluorocyclohexyl)prop-2-enoateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl(triphenylphosphoranylidene)acetate (8.827 g, 26 mmol, 1.1 eq) is added at room temperature to a solution of 4,4-difluorocyclohexanecarbaldehyde (3.55 g, 24 mmol, 1 eq) in dry THF (60 ml). The mixture is stirred for 6 h and the solvent is evaporated. Hexane (50 ml) is added to the crude, the mixture is put a few minutes in an ultrasonic bath, stirred for 1 h and filtered. The filtrate is concentrated under reduced pressure to afford 4.05 g of methyl 3-(4,4-difluorocyclohexyl)prop-2-enoate a1-16.

Workup

  1. customthe solvent is evaporated
  2. additionHexane (50 ml) is added to the crude
  3. waitthe mixture is put a few minutes in an ultrasonic bath
  4. stirringstirred for 1 h
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-17839e4b516c4ae180fd2cad427e9f7a
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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