4-Toluenesulfonyl chloride → Methyl 3-chloro-2-(methylsulfanyl)prop-2-enoate

HRID 2061023

반응식

HRID 2061023 반응식
[H-].[Na+].[CH3:3][S:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[CH:10]([O:12][CH3:13])=[O:11].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([Cl:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1>CN(C=O)C>[CH3:3][S:4][C:5](=[CH:13][O:12][S:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=1)(=[O:22])=[O:21])[C:6]([O:8][CH3:9])=[O:7].[Cl:23][CH:6]=[C:5]([S:4][CH3:3])[C:10]([O:12][CH3:13])=[O:11]

참가 물질

7

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 85522Methyl (methylthio)acetate

생성물 2

HCID 59498538Methyl 3-chloro-2-(methylsulfanyl)prop-2-enoateHCID 72308159Methyl 2-methylthio-3-(p-toluenesulfonyloxy)acrylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 21.4 g (535 mmol) of sodium hydride (60% in oil) in 200 ml of DMF was added dropwise a mixture of 25.8 g (214 mmol) of methyl 2-(methylthio)acetate and 26.5 g (428 mmol) of methyl formate under ice cooling and stirred at room temperature overnight. To the reaction mixture was added portionwise 27.0 g (141 mmol) of p-toluenesulfonyl chloride under ice cooling and stirred at room temperature for 1 hour. After dilution with tert-butyl methyl ether, the solution was washed sequentially with water and saturated NaCl solution, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain 9.72 g of methyl 2-(methylthio)-3-(p-toluenesulfonyloxy)-2-propenoate and 1.88 g of methyl 3-chloro-2-(methylthio)-2-propenoate.

후처리

  1. additionwas added dropwise
  2. stirringstirred at room temperature for 1 hour
  3. washAfter dilution with tert-butyl methyl ether, the solution was washed sequentially with water and saturated NaCl solution
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-917a295a3c904fd19d4e3edda2058cc1
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278473B2

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