Formaldehyde → HCID 11252104, compound

Participants

Reaction Conditions

Reaction Steps

(1R,5S)-6,6-Dimethylbicyclo[3.1.1]heptan-2-one (0.938 mL, 920 mg) was added to tetrahydrofuran (50 mL) and the mixture was cooled to −78° C. using an isopropanol/dry ice bath. Lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 7.99 mL) was added, and the solution was stirred at −78° C. for 15 minutes. The solution was allowed to warm to 0° C. in a water/ice bath and the mixture was stirred for 45 minutes. Paraformaldehyde (2000 mg) was added. The solution was stirred at 0° C. for 15 minutes, allowed to warm to room temperature and stir for an additional four hours. The reaction was quenched with saturated aqueous ammonium chloride, extracted with diethyl ether, washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by flash column chromatography on silica gel using 5% ethyl acetate in hexanes.

Provenance & Evidence