Diethyl 4,4-difluoroheptanedioate → Ethyl 5,5-difluoro-2-oxocyclohexane-1-carboxylate
Reaction equation
[F:1][C:2]([F:17])([CH2:10][CH2:11][C:12]([O:14]CC)=O)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].CC([O-])(C)C.[K+]>C1(C)C=CC=CC=1>[F:17][C:2]1([F:1])[CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:12](=[O:14])[CH2:11][CH2:10]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of diethyl 4,4-difluoroheptanedioate (4.3 g) in toluene (50 mL) was added potassium 2-methylpropan-2-olate (2.87 g) and the reaction stirred overnight at room temperature. The reaction was quenched with 1N aqueous HCl (100 mL) and extracted with diethyl ether (150 mL). The ether layer was washed with brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 40 g) eluting with a gradient of 1% to 5% ethyl acetate/hexanes gave the title compound.