Water → ethyl 3-(hydroxymethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate

HRID 1843097ノート

反応式

HRID 1843097 の反応式
[CH3:1][N:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([C:12]([F:15])([F:14])[F:13])[C:4]([C:16](OCC)=[O:17])=[N:3]1.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1.C1CCCCC1>[OH:17][CH2:16][C:4]1[C:5]([C:12]([F:13])([F:14])[F:15])=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:2]([CH3:1])[N:3]=1

参加物

6

反応物 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 67379138diethyl 1-methyl-4-(trifluoromethyl)-1H-pyrazole-3,5-dicarboxylate

生成物 1

HCID 58542528ethyl 3-(hydroxymethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate収率 80%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8078Cyclohexane溶媒

実験手順

A solution of 6.00 g (20.4 mmol) of diethyl 1-methyl-4-(trifluoromethyl)-1H-pyrazole-3,5-dicarboxylate in 80 ml of tetrahydrofuran is admixed under argon at −78° C. with 38.9 ml (42.8 mmol) of a 1.1M solution of diisobutylaluminium hydride in cyclohexane and stirred overnight at this temperature. The reaction mixture is admixed with water and extracted twice with ethyl acetate. The organic phase is dried over sodium sulphate, filtered over silica gel and concentrated by evaporation in vacuo. Chromatographic purification on silica gel gives 4.10 g of ethyl 3-(hydroxymethyl)-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate (80%).

後処理

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationfiltered over silica gel
  4. concentrationconcentrated by evaporation in vacuo
  5. customChromatographic purification on silica gel

出典と根拠

ORDレコード
ord-5fa13397378c4071a440bce441394cdc
出典データセット
uspto-grants-2015_02
特許番号
US08946234B2

反応ノート

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