Hydrogen Peroxide → HCID 13367858, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 24 ml of a 1M solution of lithium tri(sec-butyl)borohydride in tetrahydrofuran at -70° C. was added dropwise 3.49 g of 5,7,7-trimethyl-6-oxabicyclo[3.2.1]octan-4-one in 3 ml of tetrahydrofuran. The resulting solution was stirred under nitrogen for one hour at -70° C. and one hour at room temperature. Then while controlling the temperature at 0° C., the following were successively added: 2.6 ml of water, 5.2 ml of ethanol, 19.2 ml of 10% sodium hydroxide solution and dropwise 8.5 ml of 30% hydrogen peroxide solution. The resulting reaction mixture was stirred for one hour at 25° C., then saturated with solid potassium carbonate and extracted four times with 50 ml portions of a 1:1 solvent mixture of diethyl ether and tetrahydrofuran. The combined organic extracts were washed with 50 ml of saturated aqueous sodium chloride, dried (Na2SO4) and concentrated in vacuo to leave 6.44 g of an opaque, colorless oil. Kugelrohr distillation of the oil gave 3.13 g of the desired product as a colorless oil, b.p. 71° C. (0.35-0.15 mm), predominate (4:1) in the endo versus exo alcohol form.

Provenance & Evidence