Hydrogen Peroxide → HCID 20072998, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 8.36 g (26 mmol) of 3-Methylene-1,2-bis(benzoyloxymethyl)cyclopropane (from Step C) in tetrahydrofuran (THF) was cooled in an ice-water bath. To this solution was added 26 mL (26 mmol) of a 1 M THF solution of borane-THF complex, and the resultant solution was stirred at 5° C. for 2 h. 3N Sodium hydroxide solution (8.67 mL, 26 mmol) was then added slowly to the reaction mixture at 5° C., followed by 7.8 mL (78 mmol) of 30% aqueous hydrogen peroxide solution. The reaction mixture was stirred for 20 min at 5° C., allowed to warm to ambient temperature and stirred for 30 min at ambient temperature. The reaction mixture was diluted with ethyl acetate, washed 3 times with brine (until the pH of the aqueous layer was approximately 7) and concentrated in vacuo. The residue was purified by column chromatography on a 3×65 cm silica gel column eluted with 2% methanol in chloroform. Fractions numbered 35-47 were combined and concentrated in vacuo to give 4.1 g (46% yield) of 3-Hydroxymethyl-1,2-bis((benzoyl)oxymethyl)cyclopropane. DCI NH3MS, M/Z: 341 (M+H)+, 358 (M+NH4)+.

Provenance & Evidence