Dimethylformamide → Ethyl [(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetate

HRID 534816ノート

反応式

HRID 534816 の反応式
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[O:10].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:12][SH:13].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:9]([C:3]1[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=1[S:13][CH2:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])=[O:10]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehyde

生成物 1

HCID 63802037Ethyl [(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetate収率 28%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

A mixture of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (5.0 g), ethyl thioglycolate (3.97 g), potassium carbonate (5.53 g), and N,N-dimethylformamide (150 mL) was stirred at 80° C. for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, 90:10-50:50 hexane/ethyl acetate) to provide the title compound (2.12 g, 28%) as an oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography (silica gel, 90:10-50:50 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-999bf2ae987c468a98364e5d7f0d8ad4
出典データセット
uspto-grants-2014_10
特許番号
US08853215B2

反応ノート

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