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

HRID 1843097노트

반응식

HRID 1843097 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8078Cyclohexane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5fa13397378c4071a440bce441394cdc
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946234B2

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