Reacción #84700

Ecuación de reacción

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

ethanol

sodium hydroxide

→

compound

Rendimiento 52.0%

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

Rendimiento 52.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe resulting mixture was stirred for 3 hours
2. 2
   ConcentraciónThe 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
   Extracciónthe resulting mixture was extracted with ethyl acetate (500 mL)
5. 5
   LavadoThe organic layer was washed with water (500 mL)
6. 6
   Secadodried over anhydrous sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónfollowed by concentration under reduced pressure
9. 9
   OtroThe resultant oily matter was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10˜1:5)

Procedimiento

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.

Fuente