تفاعل #84700

معادلة التفاعل

4-iodo-6-oxa-bicyclo[3.2.1]octan-7-one

ethanol

sodium hydroxide

→

compound

المردود 52.0%

ethyl 7-oxa-bicyclo[4.1.0]heptane-3-carboxylate

المردود 52.0%

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe resulting mixture was stirred for 3 hours
2. 2
   تركيزThe reaction mixture was concentrated in a bath at a temperature of 35° C. under reduced pressure
3. 3
   workup.ADDITIONWater (500 mL) was added to the resultant oily matter
4. 4
   استخلاصthe resulting mixture was extracted with ethyl acetate (500 mL)
5. 5
   غسيلThe organic layer was washed with water (500 mL)
6. 6
   تجفيفdried over anhydrous sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزfollowed by concentration under reduced pressure
9. 9
   أخرىThe resultant oily matter was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10˜1:5)

الإجراء التجريبي

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.

المصدر