Methanol → Methyl 5-(4-fluorophenyl)-5-oxopentanoate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:21]O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:15])[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:21])=[O:13])=[CH:6][CH:7]=1Participants
4
Procedure
To a solution of 5-(4-fluorophenyl)-5-oxopentanoic acid (3.0 g, 14.3 mmol) in dry MeOH (50 ml) was added concentrated sulfuric acid (50 mg) and the mixture refluxed under nitrogen for 16 h. The bulk of the MeOH was removed by rotary evaporator and the residue treated with sodium bicarbonate solution (5%, 100 ml) and extracted with ethyl acetate (3×50 ml). The organic extract was washed with water (1×100 ml), brine (1×100 ml), dried (Na2SO4) and evaporated to give methyl 5-(4-fluorophenyl)-5-oxopentanoate (2.69 g, 84%) as a white crystalline solid.
Workup
- temperaturethe mixture refluxed under nitrogen for 16 h
- customThe bulk of the MeOH was removed by rotary evaporator
- additionthe residue treated with sodium bicarbonate solution (5%, 100 ml)
- extractionextracted with ethyl acetate (3×50 ml)
- extractionThe organic extract
- washwas washed with water (1×100 ml), brine (1×100 ml)
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-e4245208a0a8490eb9b0b044dac80ee8
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863313B2
Reaction notes
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