Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl (2E)-4,4-difluoro-4-phenylbut-2-enoate

HRID 1966626Notes

Reaction equation

HRID 1966626 reaction equation
[F:1][C:2]([F:11])([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:3]=O.[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C1COCC1>[F:1][C:2]([F:11])([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)/[CH:3]=[CH:17]/[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 14644933α,α-Difluorobenzeneacetaldehyde

Product 1

HCID 67244021Ethyl (2E)-4,4-difluoro-4-phenylbut-2-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Intermediate 19 (0.88 g, 5.64 mmol) was dissolved in THF (12 mL) and (carbethoxymethylene) triphenylphosphorane (1.96 g, 5.64 mmol) was then added. The solution was stirred at 50° C. for 12 hours. The mixture was concentrated and the residue was purified by column chromatography on silica gel using n-hexane/AcOEt (5:1) as eluent. The title compound was obtained (1.10 g, 89%) as pale yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-64f68e8880d349e9b7e1cef57995f297
Source dataset
uspto-grants-2013_04
Patent number
US08420669B2

Reaction notes

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