反应 #1851976

反应方程式

7-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Red-Al

sodium hydroxide

→

7-fluoro-2,3,4,5-tetrahydro-1,5-benzothiazepine

收率 93.0%

溶剂

toluene

反应条件

后处理

1. 1
   温度to warm to room temperature
2. 2
   温度The reaction was heated
3. 3
   温度at reflux for 1.5 hours
4. 4
   萃取extracted with dichloromethane (3×25 mL)
5. 5
   洗涤washed with water
6. 6
   干燥dried (sodium sulfate)
7. 7
   其他The concentrated organics were purified by preparative thin layer chromatography on silica gel
8. 8
   洗涤eluted with 50% ethyl acetate in hexanes

实验过程

7-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (76 mg, 0.38 mmol) dissolved in toluene (1 mL) and cooled to 0° C. in an ice bath. Red-Al (275 mL, 0.91mmol) was added and then the reaction allowed to warm to room temperature. The reaction was heated at reflux for 1.5 hours. 1 N sodium hydroxide was added slowly until pH>10, this was stirred for 10 minutes, extracted with dichloromethane (3×25 mL), washed with water, and dried (sodium sulfate). The concentrated organics were purified by preparative thin layer chromatography on silica gel and eluted with 50% ethyl acetate in hexanes to give 7-fluoro-2,3,4,5-tetrahydro-1,5-benzothiazepine (30.8 mg, 93%). 1H NMR (CDCl3, 300 MHz): δ 7.32 (t, 1H, J=7.5 Hz), 6.53-6.42 (m, 2H), 4.09 (s-broad, 1H), 3.31-3.27 (m, 2H), 2.83-2.79 (m, 2H), 2.11-2.04 (m, 2H) ppm.

来源