Dimethylformamide → Ethyl 3-(benzyloxy)-1-methyl-1H-pyrazole-4-carboxylate

HRID 1295219ノート

反応式

HRID 1295219 の反応式
[OH:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH3:12])[N:3]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:13]([O:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH3:12])[N:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178469818HCID 178469818、化合物

生成物 1

HCID 22175079Ethyl 3-(benzyloxy)-1-methyl-1H-pyrazole-4-carboxylate収率 82%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

A mixture of ethyl 3-hydroxy-1-methyl-1H-pyrazole-4-carboxylate (25.50 g), benzyl bromide (17.8 ml), potassium carbonate (31.10 g) and N,N-dimethylformamide (250 ml) was stirred overnight at 50° C. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dilute hydrochloric acid, washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-benzyloxy-1-methyl-1H-pyrazole-4-carboxylate (31.90 g, yield 82%) was obtained as a colorless crystal from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio) and recrystallized from ethyl acetate-hexane. melting point: 66–67° C.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-11786f95964a45ac9eeff59b3e79fee2
出典データセット
uspto-grants-2007_07
特許番号
US07241785B2

反応ノート

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