Hydrogen Peroxide → HCID 14699195, compound

Participants

Reaction Steps

To a solution of methyl-(E)-7-[7,9-di-(4-fluorophenyl)spiro-[4.5]deca-6,8-dien-6-yl]-5-hydroxy-3-oxo-6-heptenoate (3.0 g, 6.09 mmoles) in 80 ml of anhydrous THF was added a 1M THF solution of triethylborane (9.07 ml, 9.07 mmoles). The solution was stirred for 5 minutes at room temperature and was then cooled to -78° C. in a dry ice-acetone bath. To this mixture was added sodium borohydride (0.27 g, 7.0 mmoles) followed by the dropwise addition over 30 minutes of a solution of 6.09 ml of methanol in 15 ml of THF. The reaction was stirred for 1 hour with the temperature slowly rising to -50° C. To this mixture was added a solution of 30% hydrogen peroxide (14.17 ml) in water (7 ml) dropwise over 5 minutes. The reaction was stirred at room temperature for 1 hour and was poured into 200 ml of ethyl acetate. The mixture was extracted with 1N HCl and then brine. The organic layer was evaporated in vacuo to give 2.8 g of material. The residue was dissolved in ethyl acetate and the solution was diluted with hexane to precipitate a solid product having an m.p. of 113°-15° C. (dec).

Provenance & Evidence