反应 #92528

反应方程式

trans-androsterone

p-toluenesulfonyl chloride

→

3β-tosyloxy-5α-androstan-17-one

收率 87.0%

溶剂

pyridine

反应条件

后处理

1. 1
   其他the reaction mixture was quenched
2. 2
   workup.ADDITIONby adding H2O (10 mL) and it
3. 3
   萃取was extracted with CH2Cl2 (3×20 mL)
4. 4
   其他All organic layers were collected
5. 5
   洗涤washed over HCl (3×20 mL, 2 M), brine solution (3×20 mL), and H2O (3×20 mL)
6. 6
   干燥dried over Na2SO4
7. 7
   浓缩concentrated under reduced pressure

实验过程

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).

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