Dimethyl Sulfoxide → Butanoic acid, 2-[bis(methylthio)methylene]-3-oxo-, ethyl ester

HRID 725268노트

반응식

HRID 725268 반응식
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[C:10](=S)=[S:11].[H-].[Na+].CI.[CH3:17][S:18]([CH3:20])=O>O>[CH3:17][S:18][C:20]([S:11][CH3:10])=[C:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][CH2:8][CH3:9])=[O:6]

참가 물질

7

반응물 5

HCID 679Dimethyl Sulfoxide2회HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8868Ethyl AcetoacetateHCID 24758Sodium hydride

생성물 1

HCID 4997384Butanoic acid, 2-[bis(methylthio)methylene]-3-oxo-, ethyl ester

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 6.50 g (50.0 mmol) of ethyl acetoacetate and 4.18 g (3.30 mL, 55.0 mmol) of carbon disulfide in 60 mL of dry dimethylsulfoxide in a flame-dried 300 mL flask was treated portionwise at 16°-18° C. with 2.64 g (110 mmol) of oil-free sodium hydride. An additional 100 mL of dimethylsulfoxide was eventually added to facilitate stirring. After the addition was complete, the deep red solution was stirred for 75 minutes and then was quenched with 15.62 g (6.85 mL, 110 mmol) of methyl iodide. The reaction mixture was stirred overnight at room temperature. The solution was poured into water and extracted with ether. The extracts were washed with water, dried and evaporated to give a red oil which was used for subsequent reactions without further purification. 1H-NMR (CDCl3) δ1.24 (3H, t, J=7), 2.28 (3H, s), 2.37 (6H, s), 4.21 (2H, q, J=7).

후처리

  1. additionAfter the addition
  2. stirringthe deep red solution was stirred for 75 minutes
  3. stirringThe reaction mixture was stirred overnight at room temperature
  4. extractionextracted with ether
  5. washThe extracts were washed with water
  6. customdried
  7. customevaporated
  8. customto give a red oil which
  9. customwas used for subsequent reactions without further purification

출처 및 근거

ORD 기록
ord-200df4c64c7b4842b3992c29941ce3d8
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705646

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