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

HRID 725268ノート

反応式

HRID 725268 の反応式
[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]

参加物

7

反応物 5

HCID 679Dimethyl Sulfoxide2 回HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8868Ethyl AcetoacetateHCID 24758Sodium hydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-200df4c64c7b4842b3992c29941ce3d8
出典データセット
uspto-grants-1998_01
特許番号
US05705646

反応ノート

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