1,4-Dioxaspiro[4.5]decane-6-acetic acid, ethyl ester → 1,4-Dioxaspiro[4.5]decane-6-ethanol

Under an argon atmosphere, a solution of (±)-6-(ethoxycarbonylmethyl)-1,4-dioxaspiro[4.5]decane (1.00 g, 4.39 mmol) in diethyl ether (22 ml) was cooled to 0° C. Lithium aluminium hydride (333 mg, 8.77 mmol) was added and the mixture was stirred at room temperature for 3 h. The mixture was cooled to 0° C., quenched with ethyl acetate (10 ml) and 2 M sodium hydroxide solution (50 ml). The mixture was extracted with chloroform (3×50 ml) and the combined organic extracts were dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give the crude product which was purified using flash column chromatography with hexane-ethyl acetate (3:7) to give (±)-6-(2'-hydroxyethyl)-1,4-dioxaspiro[4.5]decane (767 mg, 94% yield) as a colourless oil. Rf 0.30 (hexane-ethyl acetate, 3:7).

1. temperatureThe mixture was cooled to 0° C.
2. customquenched with ethyl acetate (10 ml) and 2 M sodium hydroxide solution (50 ml)
3. extractionThe mixture was extracted with chloroform (3×50 ml)
4. dry with materialthe combined organic extracts were dried over magnesium sulphate
5. customThe solvent was evaporated under reduced pressure
6. customto give the crude product which
7. customwas purified

ORD record

ord-40e3f1ce80fe4a7ab13f46002a6782e4

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06140512