1-cyclohexylpropan-1-one

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: LHMDS solution (39.3 mL, 39.3 mmol, 1M in hexanes) was added to 200 mL of diethyl ether and the mixture was cooled to −78° C. Cyclohexyl ethyl ketone (5.0 g, 35.7 mmol) dissolved in 50 mL of ether was added dropwise, and the resulting mixture was stirred at −78° C. for 1 h. Diethyl oxalate (5.6 mL, 41.1 mmol) was then added dropwise, and the cooling bath was removed and the mixture was allowed to come to room temperature. After the mixture was stirred for 16 h, 1M hydrochloric acid (200 mL) was added and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (3×100 mL) and the combined organic layers were dried over MgSO4 and concentrated. The crude oil was purified by chromatography (0-20% EtOAc/hexanes) to give 5.36 g of the title compound. MS: (−) m/z 239.33 (M−1). was added dropwise the cooling bath was removed to come to room temperature After the mixture was stirred for 16 h 1M hydrochloric acid (200 mL) was added the organic layer was separated The aqueous layer was extracted with CH2Cl2 (3×100 mL) the combined organic layers were dried over MgSO4 concentrated The crude oil was purified by chromatography (0-20% EtOAc/hexanes)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: LHMDS solution (39.3 mL, 39.3 mmol, 1M in hexanes) was added to 200 mL of diethyl ether and the mixture was cooled to −78° C. Cyclohexyl ethyl ketone (5.0 g, 35.7 mmol) dissolved in 50 mL of ether was added dropwise, and the resulting mixture was stirred at −78° C. for 1 h. Diethyl oxalate (5.6 mL, 41.1 mmol) was then added dropwise, and the cooling bath was removed and the mixture was allowed to come to room temperature. After the mixture was stirred for 16 h, 1M hydrochloric acid (200 mL) was added and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (3×100 mL) and the combined organic layers were dried over MgSO4 and concentrated. The crude oil was purified by chromatography (0-20% EtOAc/hexanes) to give 5.36 g of the title compound. MS: (−) m/z 239.33 (M−1). was added dropwise the cooling bath was removed to come to room temperature After the mixture was stirred for 16 h 1M hydrochloric acid (200 mL) was added the organic layer was separated The aqueous layer was extracted with CH2Cl2 (3×100 mL) the combined organic layers were dried over MgSO4 concentrated The crude oil was purified by chromatography (0-20% EtOAc/hexanes)