반응 #51636

반응 방정식

acetic anhydride

estradiol

acetone CH2Cl2

→

diacetate

수율 95.0%

Estradiol Diacetate

수율 95.0%

용매

pyridine

반응 조건

후처리

1. 1
   기타a complete reaction
2. 2
   온도The mixture was cooled in an ice bath
3. 3
   기타the excess acetic anhydride quenched by addition of methanol (25 mL)
4. 4
   workup.STIRRINGThe mixture was stirred at 0° C. for one hour
5. 5
   온도to warm to room temperature
6. 6
   기타The solvents were removed in vacuo
7. 7
   기타the solid residue crystallized from hot methanol

실험 절차

Under nitrogen, acetic anhydride (50 mL, 264.5 mmol) was added to a solution of estradiol (1a) (20.0 g, 73.43 mmol) in dry pyridine (200 mL). The reaction mixture was stirred at room temperature overnight (16 h). The next morning, analysis by tlc (5% acetone/CH2Cl2) indicated a complete reaction. The mixture was cooled in an ice bath and the excess acetic anhydride quenched by addition of methanol (25 mL). The mixture was stirred at 0° C. for one hour and then allowed to warm to room temperature. The solvents were removed in vacuo and the solid residue crystallized from hot methanol to give the pure diacetate (2a) (24.87 g, 95%).

출처