o-Fluorobenzaldehyde → HCID 57978447, compound

HRID 2113154Notes

Reaction equation

HRID 2113154 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:17]([CH2:23][CH3:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C=CC=CC=1>C1COCC1>[CH2:23](/[C:17](=[CH:4]\[C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[F:1])/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:24]

Participants

4

Reactant 2

HCID 67970o-FluorobenzaldehydeHCID 11079329HCID 11079329, compound

Product 1

HCID 57978447HCID 57978447, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-fluorobenzaldehyde (6.2 g, 50 mmol) and ethyl 2-(triphenylphosphoranylidene)butanoate (18.8 g, 50 mmol) in THF (200 mL) was refluxed for 2 hrs. The reaction mixture was concentrated and the residue was triturated with 1:1 hexane:ethyl acetate. The precipitate was removed by filtration through silica gel and the filtrate was concentrated. The residue was purified by chromatography on silica gel eluting with 8:2 hexane:ethyl acetate to give ethyl (E)-2-ethyl-3-(2-fluorophenyl)propenoate.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was triturated with 1:1 hexane
  3. customThe precipitate was removed by filtration through silica gel
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography on silica gel eluting with 8:2 hexane

Sources & evidence

ORD record
ord-5f4e180292d54cccbd98c864cdd00ab6
Source dataset
uspto-grants-2009_04
Patent number
US07524882B2

Reaction notes

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