Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-3-(4-benzyloxy-3,5-difluoro-phenyl)-acrylic acid ethyl ester

HRID 62835Notes

Reaction equation

HRID 62835 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.[C:19]([CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:21][CH2:22][CH3:23])=[O:20]>C1COCC1>[CH2:22]([O:21][C:19](=[O:20])/[CH:24]=[CH:13]/[C:12]1[CH:15]=[C:16]([F:17])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([F:18])[CH:11]=1)[CH3:23]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 157140264-(Benzyloxy)-3,5-difluorobenzaldehyde

Product 1

HCID 90118234(E)-3-(4-benzyloxy-3,5-difluoro-phenyl)-acrylic acid ethyl esterYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Benzyloxy-3,5-difluoro-benzaldehyde (1.2 g, 4.83 mmol) obtained in Step B and carbethoxymethylene triphenylphosphorane (2.0 g, 5.78 mmol) was dissolved in THF (10 mL), and the solution was stirred at 65˜75° C. for 1 hour. After the termination of the reaction, the reactant was cooled and concentrated under reduced pressure. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/10) to obtain the title compound (1.2 g, 78%).

Workup

  1. customAfter the termination of the reaction
  2. temperaturethe reactant was cooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/10)

Sources & evidence

ORD record
ord-0bfeea6e0cdb4990ba64bd84abec8bee
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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