تفاعل #1680795

معادلة التفاعل

Isopropanol

ethyl 4-bromo-3-hydroxycyclohexanecarboxylate

H2SO4

→

Ethyl 4-bromo-3-oxocyclohexanecarboxylate

المذيبات

water

acetone

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction was stirred for 20 min
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with water
4. 4
   تجفيفbrine, was dried over MgSO4
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىPurification by chromatography on silica gel (10% EtOAc in hexane)
7. 7
   أخرىafforded 6.7 g of tide compound

الإجراء التجريبي

To a solution of ethyl 4-bromo-3-hydroxycyclohexanecarboxylate (15.06 g) in acetone (300 mL) at 0° C. was added CrO3 (12.0 g, 120 mmol), and 2 N H2SO4 (60 mL). The mixture was stirred at room temperature for 30 min. Isopropanol (15 mL) was added and the reaction was stirred for 20 min. The volume was reduced under vacuum then diluted with water and extracted with ethyl acetate. The organic layer was washed with water, then brine, was dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel (10% EtOAc in hexane) afforded 6.7 g of tide compound.

المصدر