Hydrogen Peroxide → HCID 13826445, compound

Participants

Reaction Conditions

Reaction Steps

A 1M solution of triethylborane (3.75 ml, 3.75 mmoles) was added to a solution of methyl 7-(4,7-dichloro-2-methylnaphthalen-1-yl)-5-hydroxy-3-oxo-heptanoate (0.96 g, 2.5 mmoles) in dry THF (9 ml). Air (7.5 ml) was bubbled slowly into the solution at room temperature with stirring. Stirring was continued at room temperature for 15 minutes then cooled in frozen methanol bath (-100° C.). Sodium borohydride (0.142 g, 3.75 mmoles) was added followed by the slow addition by syringe through a septum of methanol (2.7 ml) in about 10 minutes at -100° C. The reaction was stirred at -100° C. for 30 minutes. The frozen methanol bath was replaced by an ice-salt water bath and stirred for 10 minutes. Then added slowly a 30% solution of hydrogen peroxide (6.0 ml) dropwise so that the internal temperature does not exceed 5° C. Removed cooling bath and stirred at ambient temperature for 30 minutes. Made slightly acidic by the addition of 1N HCl then extracted with ethyl acetate three times. Washed the combined ethyl acetate extracts with water two times then brine, dried (MgSO4), filtered and the solvent evaporated in vacuo to leave 0.968 g of crude product which was flash chromatographed on 50×180 mm silica column eluting with 50% ethyl acetate in hexane to give 0.476 g of title compound, exact mass calc. for C18H18Cl2O3 (M-CH3OH): 352.0633; Found: 352.0638.

Provenance & Evidence