반응 #547658

반응 방정식

Triethylamine

oxalyl dichloride

3,17β-bis(benzyloxy)estra-1,3,5(10)-trien-11α-ol

dimethyl sulfoxide

→

3,17β-bis(benzyloxy)estra-1,3,5(10)-trien-11-one

용매

Dichloromethane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGby stirring for 15 minutes at −78° C
3. 3
   workup.STIRRINGwas then stirred for 5 minutes at −78° C.
4. 4
   온도warmed to room temperature
5. 5
   온도The reaction mixture was cooled again on ice
6. 6
   기타quenched by addition of ice and water
7. 7
   추출extracted with dichloromethane
8. 8
   세척The organic layer was washed with water and saturated aqueous sodium chloride
9. 9
   건조dried over anhydrous magnesium sulfate
10. 10
    여과filtered
11. 11
    농축The filtrate was concentrated under reduced pressure
12. 12
    기타an evaporator

실험 절차

Dichloromethane (92.25 ml) was added to oxalyl dichloride (3.54 ml, 40.59 mmol) under nitrogen atmosphere and the resulting mixture was cooled to −78° C. To this mixture, a solution of dimethyl sulfoxide (5.76 ml, 81.18 mmol) diluted in dichloromethane (18.45 ml) was added dropwise. After the mixture was stirred for 2 minutes at −78° C., a solution of 3,17β-bis(benzyloxy)estra-1,3,5(10)-trien-11α-ol (17.29 g, 36.90 mmol) in dichloromethane (36.90 ml) was added dropwise, followed by stirring for 15 minutes at −78° C. Triethylamine (25.7 ml, 184.5 mmol) was added dropwise to the reaction mixture, which was then stirred for 5 minutes at −78° C. and warmed to room temperature. The reaction mixture was cooled again on ice, quenched by addition of ice and water, and then extracted with dichloromethane. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure using an evaporator to give crude 3,17β-bis(benzyloxy)estra-1,3,5(10)-trien-11-one (crude 18.76 g, quant from crude 1H-NMR).

출처