Ethanol → Ethyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate

To a suspension of Racemate-4-iodo-6-oxa-bicyclo[3.2.1]octan-7-one (45.0 g, 180 mmol) in ethanol (400 mL) was added 2 N aqueous sodium hydroxide (110 mL, 220 mmol) at room temperature while being stirred, and the resulting mixture was stirred for 3 hours. The reaction mixture was concentrated in a bath at a temperature of 35° C. under reduced pressure. Water (500 mL) was added to the resultant oily matter, and the resulting mixture was extracted with ethyl acetate (500 mL). The organic layer was washed with water (500 mL), dried over anhydrous sodium sulfate, filtered and followed by concentration under reduced pressure. The resultant oily matter was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10˜1:5), to thereby give the tile compound (15.9 g, 52%) as a pale yellow oil.

1. stirringthe resulting mixture was stirred for 3 hours
2. concentrationThe reaction mixture was concentrated in a bath at a temperature of 35° C. under reduced pressure
3. additionWater (500 mL) was added to the resultant oily matter
4. extractionthe resulting mixture was extracted with ethyl acetate (500 mL)
5. washThe organic layer was washed with water (500 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationfollowed by concentration under reduced pressure
9. customThe resultant oily matter was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10˜1:5)

ORD record

ord-d301b167702a4d90aa832036daab9239

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434700B2