3-Fluorobenzaldehyde → Ethyl 3-(3-fluorophenyl)-2-propenoate

HRID 322069Notes

Reaction equation

HRID 322069 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C1(P(=[CH:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

4

Reactant 2

HCID 680093-FluorobenzaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 367202Ethyl 3-(3-fluorophenyl)-2-propenoateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluorobenzaldehyde 1-1 (18.16 g, 146 mmol) in dichloromethane (500 mL) was added ethyl (triphenylphosphoranylidene)acetate (61.2 g; 176 mmol) and the resulting solution was stirred at room temperature for 18 hr. After evaporation of the solvent, the residue was swirled with ether/hexane and filtered. The filtrate was concentrated and then purified on a plug of silica gel eluting with hexane/EtOAc 9:1. Removal of the solvent afforded the title compound 1-2 as an oil (˜95% trans) which was used without further purification in the next step.

Workup

  1. customAfter evaporation of the solvent
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified on a plug of silica gel eluting with hexane/EtOAc 9:1
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-d3ed122d640745c68777acd05840912f
Source dataset
uspto-grants-2001_04
Patent number
US06211191B1

Reaction notes

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