Реакция #76277

Уравнение реакции

methanol

LiBH4

ammonium chloride

3-(3-{2-[3-(2-ethoxycarbonyl-2-methyl-propyl)-phenyl]-[1,3]dithian-2-yl }-phenyl)-2,2-dimethyl-propanoic acid ethyl ester

→

3-(3-{2-[3-(3-hydroxy-2,2-dimethyl-propyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethyl-propan-1-ol

Выход 85.9%

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was heated
2. 2
   Температураto reflux for 6 h
3. 3
   ДругоеThe layers were separated
4. 4
   Экстракцияthe aqueous layer was extracted with dichloromethane (2×10 mL)
5. 5
   СушкаThe combined organic phases were dried over sodium sulfate
6. 6
   Концентрированиеconcentrated in vacuo

Методика

To a suspension of LiBH4 (0.78 g, 33 mmol) in dichloromethane (55 mL) was added methanol (1.04 g, 33 mmol) at rt. After the addition of 3-(3-{2-[3-(2-ethoxycarbonyl-2-methyl-propyl)-phenyl]-[1,3]dithian-2-yl }-phenyl)-2,2-dimethyl-propanoic acid ethyl ester (6.5 g, 12.2 mmol), the reaction mixture was heated to reflux for 6 h. After cooling to rt, saturated ammonium chloride solution (20 mL) and dichloromethane (15 mL) were added. The layers were separated and the aqueous layer was extracted with dichloromethane (2×10 mL). The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford crude 3-(3-{2-[3-(3-hydroxy-2,2-dimethyl-propyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethyl-propan-1-ol (4.66g, 85%) as an oil. 1H NMR (300 MHz, CDCl3): δ (ppm): 7.6-6.8 (m, 8H), 3.63 (s, 4H), 3.16 (s, 4H), 2.95-2.60 (m, 4H), 2.0-1.8 (m, 2H), 1.61 (s, 2H), 0.75 (s, 12H). 13C NMR (75 MHz, CDCl3): δ (ppm): 142.4, 139.2, 131.7, 128.9, 128.1, 127.0, 71.1, 44.9, 43.7, 36.7, 29.6, 27.3, 24.2.

Источник