تفاعل #92528

معادلة التفاعل

trans-androsterone

p-toluenesulfonyl chloride

→

3β-tosyloxy-5α-androstan-17-one

المردود 87.0%

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction mixture was quenched
2. 2
   workup.ADDITIONby adding H2O (10 mL) and it
3. 3
   استخلاصwas extracted with CH2Cl2 (3×20 mL)
4. 4
   أخرىAll organic layers were collected
5. 5
   غسيلwashed over HCl (3×20 mL, 2 M), brine solution (3×20 mL), and H2O (3×20 mL)
6. 6
   تجفيفdried over Na2SO4
7. 7
   تركيزconcentrated under reduced pressure

الإجراء التجريبي

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).

المصدر