Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetate → 4,4-Difluoro-4-(4'-methoxy-biphenyl-4-yl)-butyric Acid

HRID 23759Notes

Reaction equation

HRID 23759 reaction equation
C([O:3][C:4](=[O:24])[CH:5]=[CH:6][C:7]([F:23])([F:22])[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)C.C1(P(=CC(OCC2C=CC=CC=2)=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[F:22][C:7]([F:23])([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH2:6][CH2:5][C:4]([OH:24])=[O:3]

Participants

4

Reactant 2

HCID 3862746Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetateHCID 697848674,4-Difluoro-4-(4'-methoxy-biphenyl-4-yl)-but-2-enoic acid ethyl ester

Product 1

HCID 98395084,4-Difluoro-4-(4'-methoxy-biphenyl-4-yl)-butyric Acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4,4-Difluoro-4-(4′-methoxy-biphenyl-4-yl)-but-2-enoic acid ethyl ester. A solution of benzyl (triphenylphosphoranylidene)acetate (320 mg, 0.779 mmol) and 2,2-difluoro-2-(4′-methoxy-4-biphenyl)acetaldehyde (198 mg, 0.755 mmol) in toluene (4 mL) is heated to 90° C. with stirring for 2 hours. The reaction is cooled to room temperature and concentrated under reduced pressure. The crude product is purified by column chromatography (silica gel, 20% EtOAc/hexanes) to give the desired product as a pale yellow oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product is purified by column chromatography (silica gel, 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6f32d99f6e1f4661b04b1db88d46b76b
Source dataset
uspto-grants-2005_02
Patent number
US06852751B2

Reaction notes

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