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

HRID 1830123노트

반응식

HRID 1830123 반응식
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]

참가 물질

5

반응물 3

HCID 7761Diethyl MalonateHCID 11430Potassium Carbonate2회HCID 141124502-Iodoethylphenyl sulfide

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
52 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ec49d261e4ba4dca99ee4de51b62dcc3
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07064123B1

반응 노트

불러오는 중…