반응 #92528

반응 방정식

trans-androsterone

p-toluenesulfonyl chloride

→

3β-tosyloxy-5α-androstan-17-one

수율 87.0%

용매

pyridine

반응 조건

후처리

1. 1
   기타the reaction mixture was quenched
2. 2
   workup.ADDITIONby adding H2O (10 mL) and it
3. 3
   추출was extracted with CH2Cl2 (3×20 mL)
4. 4
   기타All organic layers were collected
5. 5
   세척washed over HCl (3×20 mL, 2 M), brine solution (3×20 mL), and H2O (3×20 mL)
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated under reduced pressure

실험 절차

In a 25 mL round bottom flask, trans-androsterone (1.00 g, 3.44 mmol) and p-toluenesulfonyl chloride (1.51 g, 7.91 mmol) was dissolved in in pyridine (4.30 mL). The reaction mixture was stirred continuously at room temperature. After 24 h, the reaction mixture was quenched by adding H2O (10 mL) and it was extracted with CH2Cl2 (3×20 mL). All organic layers were collected, combined together and washed over HCl (3×20 mL, 2 M), brine solution (3×20 mL), and H2O (3×20 mL), dried over Na2SO4, and concentrated under reduced pressure afforded 3β-tosyloxy-5α-androstan-17-one (1.33 g, 87%) as a white solid. 1H NMR (300 MHz, CDCl3): d 7.79 (dt, J=8.3, 1.9 Hz, 2H), 7.33 (dd, J=8.0, 0.5 Hz, 2H), 4.42 (h, J=5.9 Hz, 1H), 2.44 (s, 3H), 2.38-2.47 (m, 1H), 1.99-2.11 (m, 1H), 1.86-1.95 (m, 1H), 1.78-1.80 (m, 1H), 1.71-1.77 (m, 2H), 1.65-1.69 (m, 1H), 1.56-1.64 (m, 3H), 1.44-1.55 (m, 3H), 1.30-1.31 (m, 1H), 1.28-1.29 (m, 2H), 1.22-1.24 (m, 1H), 1.18-1.20 (m, 1H), 1.04-1.16 (m, 1H), 0.85-1.00 (m, 2H), 0.84 (s, 3H), 0.80 (s, 1H), 0.60-0.69 (m, 1H).

출처