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Water → Methyl 2-chloro-3-oxoheptanoate

HRID 1983551
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HRID 1983551 반응식
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9].S(Cl)([Cl:15])(=O)=O.O>ClCCl>[CH3:1][O:2][C:3](=[O:11])[CH:4]([Cl:15])[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9]
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참가 물질

5

반응물 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 546075Methyl 3-oxoheptanoate

생성물 1

HCID 57713025Methyl 2-chloro-3-oxoheptanoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5.0 g 3-Oxo-heptanoic acid methyl ester were dissolved in 80 ml dry dichloromethane and 2.82 ml sulfurylchloride were added. The reaction mixture was stirred at room temperature for 30 minutes. 20 ml of water were added and the reaction mixture extracted five times with portions of 30 ml of dichloromethane. The combined organic extracts were washed with water and saturated NaHCO3 solution and brine and dried over MgSO4. The solvent was removed under reduced pressure to obtain 6.0 g 2-Chloro-3-oxo-heptanoic acid methyl ester as raw material. This material was used without further purification. 6.0 g 2-Chloro-3-oxo-heptanoic acid methyl ester were dissolved in 50 ml ethanol and 6.4 g 4-(Trifluoromethyl)thiobenzamide were added. The reaction mixture was heated under reflux overnight. The solvent was removed under reduced pressure and the residue purified by chromatography with the eluent n-heptane:ethyl acetate=100:1=>60:1. This gives 7.4 g 4-Butyl-2-(4-trifluoromethylphenyl)-thiazol-5- carboxylic acid methyl ester as yellow oil.

후처리

  1. extractionthe reaction mixture extracted five times with portions of 30 ml of dichloromethane
  2. washThe combined organic extracts were washed with water and saturated NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-91c239f6b9ba45b6a40b7928487e8548
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07541464B2

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