A kind of synthetic method of 25-hydroxy-7-dehydrocholesterol
A technique for the synthesis of dehydrocholesterol, which is applied in the fields of steroids and organic chemistry, can solve the problems of cumbersome steps, achieve high reaction efficiency, good reaction selectivity, and avoid recovery operations
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Embodiment 1
[0022] At room temperature, 5.0 g (10 mmol) of 25-hydroxy-7-ketocholesterol diacetate (R 1 =R 2 =Ac), 2.05g (11 mmol) p-toluenesulfonyl hydrazide, 1.19g (22 mmol) sodium methoxide were successively added into the ball milling tank, and the ball milling reaction was carried out for 0.5 hours. After the reaction, the reaction mixture was washed and filtered with 20 mL of water, and the filtered Add the cake to 25mL ethanol (95%) to dissolve, add sodium hydroxide, control the pH value ≥ 13, react at 50°C for 1 hour, cool down to room temperature to crystallize, filter to obtain a light yellow solid, and then recrystallize with ethanol to obtain a white tablet Crystalline, 25-hydroxy-7-dehydrocholesterol 3.52g, yield 88%, melting point 191~193℃, 1 H NMR (400 MHz, CDCl 3 ) δ = 5.55 - 5.57 (m, 1H), 5.36 - 5.39 (m, 1H), 3.59-3.67 (m,1H), 2.44 - 2.49 (m, 1H), 2.25 - 2.31(m, 1H), 2.06 - 2.11(m, 1H), 1.87 - 1.99(m, 4H), 1.54 - 1.75 (m, 7H), 1.26 - 1.51 (m, 11H), 1.22 (s, 6H), 1.02 - ...
Embodiment 2
[0024] At room temperature, 5.0 g (10 mmol) of 25-hydroxy-7-ketocholesterol diacetate (R 1 =R 2 =Ac), 2.05g (11 mmol) p-toluenesulfonyl hydrazide, 0.18g (22 mmol) lithium hydride were successively added into the ball milling tank, and the ball milling reaction was carried out for 0.5 hours. After the reaction, the reaction mixture was washed and filtered with 20 mL of water, and the filtered Add the cake to 25mL ethanol (95%) to dissolve, add sodium hydroxide, control the pH value ≥ 13, react at 50°C for 1 hour, cool down to room temperature to crystallize, filter to obtain a light yellow solid, and then recrystallize with ethanol to obtain a white tablet 25-hydroxy-7-dehydrocholesterol 3.48g, yield 87%, melting point 191~193℃.
Embodiment 3
[0026] At room temperature, 5.0 g (10 mmol) of 25-hydroxy-7-ketocholesterol diacetate (R 1 =R 2 =Ac), 2.05g (11 mmol) p-toluenesulfonyl hydrazide, 0.86g (22 mmol) sodium amide were successively added to the ball milling tank, and the ball milling reaction was 0.5 hours. After the reaction, the reaction mixture was washed and filtered with 20 mL of water, and the filtered Add the cake to 25mL ethanol (95%) to dissolve, add sodium hydroxide, control the pH value ≥ 13, react at 50°C for 1 hour, cool down to room temperature to crystallize, filter to obtain a light yellow solid, and then recrystallize with ethanol to obtain a white tablet 25-hydroxy-7-dehydrocholesterol 3.56g, yield 89%, melting point 191~193℃.
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