Ethyl 2-(triphenylphosphoranylidene)propionate → (E)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-methylacrylate

HRID 2069597Notes

Reaction equation

HRID 2069597 reaction equation
[CH2:1]([O:8][C:9]1[C:16]([F:17])=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([O:21][C:22]([C:24](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:25])=[O:23])[CH3:20]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:16]([F:17])=[CH:15][C:12](/[CH:13]=[C:24](\[CH3:25])/[C:22]([O:21][CH2:19][CH3:20])=[O:23])=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 79792Ethyl 2-(triphenylphosphoranylidene)propionateHCID 157140264-(Benzyloxy)-3,5-difluorobenzaldehyde

Product 1

HCID 59419841(E)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-methylacrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(benzyloxy)-3,5-difluorobenzaldehyde (7) (1.32 g, 5.34 mmol) and (1-ethoxycarbonylethylidene)triphenyl phosphorane (2.32 g, 6.41 mmol) in tetrahydrofuran (53 mL) was refluxed for 2 hours. The reaction was concentrated in vacuo and was purified by flash column chromatography (0-100% EtOAc in hexanes) to give (E)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-methylacrylate (8).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customwas purified by flash column chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d3f39afbd1f741518a532d05a8bed9f6
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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