Реакция #87334

Уравнение реакции

ketone

17-(1H-Benzimidazol-1-yl)-androsta-4,16-dien-3-one

MeLi

→

product 40

Выход 48.0%

3-Methyl-3-hydroxy-17-(1H-benzimidazol-1-yl)-androsta-4,16-diene

Выход 48.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.WAITroom temperature for 3 h
2. 2
   ДругоеThe reaction was quenched with saturated aqueous NH4Cl
3. 3
   Экстракцияwas extracted with EtOAc
4. 4
   ПромывкаThe organic layer was washed with brine
5. 5
   Сушкаdried over Na2SO4
6. 6
   Другоеthe solvent was removed under vacuum
7. 7
   ДругоеThe residue was purified by short FCC [petroleum ether, EtOAc, TEA (60:40:0.5)]

Методика

To a solution of ketone (32) (0.1 g, 0.26 mmol) in dry THF (3 mL) was added MeLi (1.6 M solution in ether, 0.41 mL, 0.60 mmol) at −60° C., and the resulting mixture was stirred at 0° C. for 1 h then room temperature for 3 h. The reaction was quenched with saturated aqueous NH4Cl and was extracted with EtOAc. The organic layer was washed with brine and dried over Na2SO4, and the solvent was removed under vacuum. The residue was purified by short FCC [petroleum ether, EtOAc, TEA (60:40:0.5)] to afford product 40 (0.05 g, 48%); mp 95-97° C.; IR (Neat) 3329, 2827, 2853, 1489, 1453, 1376, 1292, 1226, 1133, 918, 741 cm−1; 1H NMR (500 MHz, CDCl3) δ 1.00 (s, 3H, 18-CH3), 1.07 (s, 3H, 19-CH3), 1.27 (s, 3H, C3-CH3), 5.25 (t, J=1.6 Hz, 1H, 6-H), 5.96 (t, 1H, J=1.52 Hz, 16-H), 7.29 (m, 2H, aromatic-Hs), 7.49 (m, 1H, aromatic-H), 7.82 (dd, J=7.0, 2.6 Hz, 1H, aromatic-H), and 7.95 (s, 1H, 2′-H); 13C NMR (500 MHz, CDCl3) δ 145.3, 127.6, 124.4, 123.6, 122.7, 120.4, 111.4, 70.1, 55.7, 54.8, 37.8, 35.6, 35.3, 34.7, 32.5, 30.4, 28.5, 21.1, 18.8, 16.3. HRMS calcd 425.2563 (C27H34ON2.Na+). found 425.2570.

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