Methanol → 4,4,4-Trifluoro-1-(4-pyrazol-1-yl-phenyl)-butane-1,3-dione

HRID 1855361

反応式

HRID 1855361 の反応式
C[O-].[Na+].CO.[F:6][C:7]([F:14])([F:13])[C:8]([O:10]CC)=O.[N:15]1([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[CH:22][CH:21]=2)[CH:19]=[CH:18][CH:17]=[N:16]1>C(OC(C)(C)C)C>[F:14][C:7]([F:6])([F:13])[C:8](=[O:10])[CH2:27][C:26]([C:23]1[CH:22]=[CH:21][C:20]([N:15]2[CH:19]=[CH:18][CH:17]=[N:16]2)=[CH:25][CH:24]=1)=[O:28]

参加物

6

反応物 4

HCID 887MethanolHCID 9794Ethyl trifluoroacetateHCID 10942334Sodium MethoxideHCID 122381341-[4-(1H-pyrazol-1-yl)phenyl]ethan-1-one

生成物 1

HCID 686309374,4,4-Trifluoro-1-(4-pyrazol-1-yl-phenyl)-butane-1,3-dione収率 63.4%

試薬・触媒・溶媒 1

HCID 12512Ethyl tert-butyl ether溶媒2 回

反応条件

温度
20 °C

実験手順

A 5.4 N solution of sodium methoxide in methanol (3.0 mL, 16.2 mmol) was added drop wise over 10 min to a solution of ethyl trifluoro-acetate (1.81 mL, 15.2 mmol) in 2-ethoxy-2-methyl-propane (20 mL) at 20° C. followed by the addition of a suspension of 1-(4-pyrazol-1-yl-phenyl)-ethanone (2.57 g, 13.8 mmol) in 2-ethoxy-2-methyl-propane (10 mL). The reaction mixture was stirred for 22 h at 20° C. and then poured onto ice-water (50 mL). The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The remaining solid was recrystallized from ethyl acetate/heptane to give the title compound (2.47 g, 63%) as off-white solid. Mp 96° C.

後処理

  1. additionpoured onto ice-water (50 mL)
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe remaining solid was recrystallized from ethyl acetate/heptane

出典と根拠

ORDレコード
ord-35d4d44f7e334382a8d9b1f824d5df5c
出典データセット
uspto-grants-2015_02
特許番号
US08962834B2

関連ノート

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