1,2-Cyclohexanedimethanol → (3Ar,7as)-hexahydro-2-benzofuran-1(3h)-one

Temperature

0 °C

There were weighed out 1,2-bis(hydroxymethyl)cyclohexane (7, meso compound) (144 mg, 1.00 mmol) and (S)-(−)-3,3,5,5-tetramethyl-4H-dinaphtho[2,1-c:1′,2′-e]-azepin-N-oxyl (3.0 mg, 1.00 mmol). Then, 2 ml of acetone was added to obtain a uniform solution. Two platinum electrodes (1.5×1.0 cm) were applied to the solution which was then subjected to an electrolytic oxidation reaction for 4 hours while being vigorously stirred at 0° C. and maintaining the current at 30 mA (quantity of electricity being 4.5 F/mol). After completion of reaction, silica gel was filtered off from the reaction mixture, extraction was effected with 5 ml of acetone and acetone was distilled off. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=7/1), giving (1R, 6S)-8-oxabicyclo[4.3.0]nonan-7-one (8) (cis lactone) (122 mg, yield 92%, optical purity 85%).

1. customto obtain a uniform solution
2. customwas then subjected to an electrolytic oxidation reaction for 4 hours
3. temperaturemaintaining the current at 30 mA (quantity of electricity being 4.5 F/mol)
4. customAfter completion of reaction, silica gel
5. filtrationwas filtered off from the reaction mixture, extraction
6. distillationwas distilled off
7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=7/1)

ORD record

ord-259c792ef5454167b3f7d4e67782cb6c

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183421B2