反応 #79590

反応方程式

bromoacetonitrile

product

[9-benzyl-4-carbamoyl-7-methoxy-1,2,3,4-tetrahydrocarbazol-5-yl]oxyacetic acid sodium salt

dimethylformamide

sodium hydride

→

titled product

9-benzyl-7-methoxy-5-cyanomethyloxy-1,2,3,4-tetrahydrocarbazole-4-carboxamide

溶媒

tetrahydrofuran

ethyl acetate

反応条件

後処理

1. 1
   洗浄washed with water
2. 2
   洗浄washed with brine
3. 3
   乾燥dried over sodium sulfate
4. 4
   その他evaporated in vacuo
5. 5
   その他The residue was chromatographed on silica gel eluting with a gradient of 0 to 4% methanol in methylene chloride

実験手順

A solution of 1.47 gram (4.19 mmol) of the product from Example 3, Part A in 146 ml. of dimethylformamide and 31 ml. tetrahydrofuran was treated with 210 mg. of sodium hydride (60% in mineral oil; 5.24 mmol) for 10 minutes and then with 0.39 ml. (0.66 mmol) of bromoacetonitrile for 3.5 hours. The mixture was diluted with ethyl acetate, washed with water, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a gradient of 0 to 4% methanol in methylene chloride to give the titled product, 1.34 gram, 82%.

出典