Diethyl Malonate → 2,2-Bis-(2-phenylsulfanyl-ethyl)-malonic acid diethyl ester

HRID 1830123ノート

反応式

HRID 1830123 の反応式
I[CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:11]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:20]([O:19][C:11](=[O:18])[C:12]([CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:21]

参加物

5

反応物 3

HCID 7761Diethyl MalonateHCID 11430Potassium Carbonate2 回HCID 141124502-Iodoethylphenyl sulfide

生成物 1

HCID 694375232,2-Bis-(2-phenylsulfanyl-ethyl)-malonic acid diethyl ester収率 43.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
52 °C

実験手順

A mixture of 2-iodoethylphenyl sulfide (19.81 g, 75 mmol), diethyl malonate (4.80 g, 30 mmol), potassium carbonate (10.35 g, 75 mmol) and DMF (40 mL) was heated at 52° C. for 18 hours. More potassium carbonate (10 g) was added and the reaction was continued at 52° C. for another 8 hours. The reaction mixture was cooled, diluted with ice water and the product extracted with ethyl acetate. The extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure and the residue was chromatographed on silica gel eluting with ethyl acetate/hexane to give 2,2-bis-(2-phenylsulfanyl-ethyl)-malonic acid diethyl ester (5.648 g).

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionthe product extracted with ethyl acetate
  3. washThe extracts were washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by rotary evaporation at reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-ec49d261e4ba4dca99ee4de51b62dcc3
出典データセット
uspto-grants-2006_06
特許番号
US07064123B1

反応ノート

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