Cycloate → 6-Methoxy-1-oxaspiro[2,5]octane

To a stirred suspension of sodium hydride (60% in mineral oil, 1.20 g, 30.0 mmol) in dimethylsulfoxide (19 mL) was added trimethylsulfoxonium iodide (6.89 g, 31.3 mmol) at room temperature, and the mixture was stirred at room temperature for 30 min. To this mixture was added a solution of 4-methoxycyclohexanone (3.53 g, 10.0 mmol, prepared according to Shvily, Ronit et al., J. Chem. Soc. Perkin Trans. 2, 1997, 6, 1221) in dimethylsulfoxide (95 mL) dropwise at room temperature, and the mixture was stirred at room temperature for 20 h. Then the mixture was diluted with water (1.0 L), and extracted with diethyl ether (200 mL×6). The combined organic layers were dried over magnesium sulfate, and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting n-hexane/ethyl acetate (v/v=15/1˜10/1) to give 338 mg (9%, cis) and 204 mg (5%, trans) of the title compound as colorless oil respectively.

1. customprepared
2. extractionextracted with diethyl ether (200 mL×6)
3. dry with materialThe combined organic layers were dried over magnesium sulfate
4. concentrationconcentrated in vacuo
5. customThe residue was chromatographed on a column of silica gel
6. washeluting n-hexane/ethyl acetate (v/v=15/1˜10/1)

ORD record

ord-c7b290177d6340a1b494980bf6f5a1b5

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362038B2