Methanol → 5-(4-Fluoro-phenyl)-pentanoic acid methyl ester

HRID 2100506Notes

Reaction equation

HRID 2100506 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1.O.[CH3:20]O>>[CH3:20][O:17][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([F:5])=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 27346705-(4-Fluorophenyl)pentanoic acid

Product 1

HCID 685705095-(4-Fluoro-phenyl)-pentanoic acid methyl esterYield 75%

Procedure

Thionylchloride (288 μl, 3.98 mmol) was added dropwise to a solution of 5-(4-fluoro-phenyl)-pentanoic acid (520 mg, 2.65 mmol) in methanol (11 ml) at −15° C. The reaction mixture was then stirred at room temperature for 1.5 h. Water was added and the mixture was extracted 3 times with diethylether. The combined extracts were washed with water and brine, dried (Na2SO4) and evaporated. The remaining residue was purified by column chromatography (silica gel, ethyl acetate/heptane 5:95 to 12:88) to obtain 5-(4-fluoro-phenyl)-pentanoic acid methyl ester (420 mg, 2 mmol; 75%) as colorless liquid. MS: m/e 211.0 [M+H+].

Workup

  1. extractionthe mixture was extracted 3 times with diethylether
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe remaining residue was purified by column chromatography (silica gel, ethyl acetate/heptane 5:95 to 12:88)

Sources & evidence

ORD record
ord-27480444f9d347468d44545597e2c8dc
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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