Bromoacetonitrile → ethyl 1-(cyanomethyl)-5-methyl-1H-pyrrole-2-carboxylate

HRID 77363

반응식

HRID 77363 반응식
[CH3:1][C:2]1[NH:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:15][C:16]#[N:17]>CN(C)C=O.C(OCC)(=O)C>[C:16]([CH2:15][N:6]1[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:17]

참가 물질

6

반응물 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 965981H-Pyrrole-2-carboxylic acid, 5-methyl-, ethyl ester

생성물 1

HCID 86706662ethyl 1-(cyanomethyl)-5-methyl-1H-pyrrole-2-carboxylate수율 39.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of ethyl 5-methyl-1H-pyrrole-2-carboxylate (1 g, 6.53 mmol) in anhydrous N,N-dimethylformamide (20 mL) under nitrogen at 0° C. was treated with a 60% dispersion of sodium hydride in mineral oil (392 mg, 9.79 mmol). After effervescence ceased, the reaction was treated with a solution of 2-bromoacetonitrile (1.17 g, 9.79 mmol) in N,N-dimethylformamide (2 mL). The resulting mixture was allowed to warm to room temperature and was stirred at room temperature for 30 min. At this time, the reaction was diluted with ethyl acetate (200 mL), washed with water (2×100 mL) and a saturated aqueous sodium chloride solution (2×100 mL), dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (80 g silica gel column, 0-20% ethyl acetate/hexanes) afforded ethyl 1-(cyanomethyl)-5-methyl-1H-pyrrole-2-carboxylate (0.5 g, 39.8%). LC-MS calcd. for C10H13N2O2 [(M+H+] 193, obsd. 193.1.

후처리

  1. washwashed with water (2×100 mL)
  2. dry with materiala saturated aqueous sodium chloride solution (2×100 mL), dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a8e6857b07574fe5b2a7a3e665fe38ee
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841299B2

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