8-(nitromethyl)-1,4-dioxaspiro[4.5]decan-8-ol synthesis

Yield:879514-21-3 40%

Reaction Conditions:

with sodium ethanolate in ethanol at 20; for 120 h;

Steps:

9.A

To a solution of 1,4-cyclohexanedione mono-ethylene ketal (30.0 g, 192 mmol) and nitromethane (15.6 mL, 288 mmol) in ethanol (18 mL) was added a solution of sodium ethoxide in ethanol (2.67 M, 3.4 mL, 9.6 mmol). The solution was stirred at room temperature (rt) for 5 days (d), then was concentrated under reduced pressure to a brown oil that was partitioned between water (100 mL) and dichloromethane (100 mL). The aqueous layer was extracted with dichloromethane (3 x 100 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated to a light brown oil. Purification by flash chromatography (silica gel, 40% ethyl acetate/hexanes) provided the product 8- (nitromethyl)-l,4-dioxaspiro[4.5]decan-8-ol as a clear oil (16.7 g, 40%) that slowly formed clear crystals overnight.

References:

WO2006/28545,2006,A2 Location in patent:Page/Page column 99