o-Fluorostyrene → 10-(2-Fluoro-phenyl)-dec-9-enoic acid ethyl ester

HRID 1802979

Reaction equation

HRID 1802979 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[CH3:2].[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1C=C>ClCCl>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=1[F:15])[CH3:2]

Participants

4

Reactant 2

HCID 123056o-FluorostyreneHCID 522255Ethyl 9-decenoate

Product 1

HCID 6687504210-(2-Fluoro-phenyl)-dec-9-enoic acid ethyl esterYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 9-decenoic acid ethyl ester (Tetrahedron 2003, 59, 7973; 500 mg, 2.53 mmol) and 2-fluorostyrene (617 mg, 5.05 mmol) in dichloromethane (12.5 mL) was added dichloro(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)(phenylmethylene)(tri-cyclohexylphosphine)ruthenium (107 mg, 0.13 mmol). The mixture was flushed with nitrogen and sealed in a pressure tube, then heated at 40° C. for 18 h. After cooling and evaporation of the solvent, the product was purified by chromatography (SiO2, heptane-dichloromethane 3:1) to afford 10-(2-fluoro-phenyl)-dec-9-enoic acid ethyl ester (420 mg, 57%).

Workup

  1. customThe mixture was flushed with nitrogen
  2. customsealed in a pressure tube
  3. temperatureAfter cooling
  4. customevaporation of the solvent
  5. customthe product was purified by chromatography (SiO2, heptane-dichloromethane 3:1)

Sources & evidence

ORD record
ord-2d0de54487254874b94806b6b639511c
Source dataset
uspto-grants-2013_01
Patent number
US08349893B2

Linked notes

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