Ethanol → HCID 13732939, compound

Participants

Reaction Steps

A mixture of 7.48 g of spiro[benzofuran-2(3H),1'-cycloheptan]-3-one, 175 ml of denatured ethanol and 1.31 g of sodium borohydride was stirred for 23 hours at room temperature under nitrogen. After addition of 250 ml of distilled water and 10-15 minutes of stirring, the mixture was partitioned between 250 ml of distilled water and 250 ml of ether. The phases were separated and the aqueous phase extracted with additional ether (2×250 ml). The combined organic extracts were washed with distilled water (250 ml) and saturated sodium chloride solution (250 ml) and thereafter dried over anhydrous sodium sulfate. Filtration and concentration in vacuo afforded a solid which was triturated, filtered and washed with hexane. The filtrate was concentrated in vacuo to afford a second crop. Trituration and washing with hexane were repeated to afford in two crops 6.75 g of a crystalline solid, m.p. 104°-107° C.

Provenance & Evidence