반응 #79590

반응 방정식

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

용매

tetrahydrofuran

ethyl acetate

반응 조건

후처리

1. 1
   세척washed with water
2. 2
   세척washed with brine
3. 3
   건조dried over sodium sulfate
4. 4
   기타evaporated in vacuo
5. 5
   기타The residue was chromatographed on silica gel eluting with a gradient of 0 to 4% methanol in methylene chloride

실험 절차

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%.

출처