Water → Spiro(4.5)decan-6-one

Temperature

0 °C

Cyclohexanone (3.0 mL) was dissolved in toluene (60 mL), and cooled to 0° C. in nitrogen atmosphere. Potassium tert-butoxide (6.86 g) was added to the reaction mixture at 0° C. and stirred for 30 minutes. To the resulting suspension, 1,4-dibromomethane (3.65 mL) was added, and then the reaction mixture was stirred at 150° C. for 6 hours. Cooling the reaction mixture to room temperature, water was added thereto, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, the solvent was removed by distillation, and the resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate=50/1) to provide 690.0 mg of the title compound as a colorless, oily substance.

1. stirringthe reaction mixture was stirred at 150° C. for 6 hours
2. temperatureCooling the reaction mixture to room temperature
3. extractionfollowed by extraction with ethyl acetate
4. dry with materialThe extract was dried over anhydrous magnesium sulfate
5. customthe solvent was removed by distillation
6. customthe resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate=50/1)

ORD record

ord-47e2f9ba40974fea8e2a7fee0df0a151

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07300947B2