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

HRID 77363

反応式

HRID 77363 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a8e6857b07574fe5b2a7a3e665fe38ee
出典データセット
uspto-grants-2014_09
特許番号
US08841299B2

関連ノート

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