Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(2-fluoro-5-methoxyphenyl)acrylate

HRID 709699Notes

Reaction equation

HRID 709699 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=O.C1(P(=[CH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[CH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 77260531Ethyl 3-(2-fluoro-5-methoxyphenyl)acrylateYield 38.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-fluoro-5-methoxybenzaldehyde (1.54 g) in toluene (50 mL) was added ethyl (triphenylphosphoranylidene)acetate (3.83 g), and the mixture was stirred at 70° C. for 15 hr. The reaction mixture was concentrated, and diethyl ether was added. The insoluble material was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (862 mg) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiethyl ether was added
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f6dfcdb008d34d4496d69fd0a6db49d4
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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