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Water → Methyl 2-chloro-3-oxoheptanoate

HRID 2233545
Notes
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Reaction equation

HRID 2233545 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 546075Methyl 3-oxoheptanoate

Product 1

HCID 57713025Methyl 2-chloro-3-oxoheptanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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-trifluoromethyl-phenyl)-thiazol-5-carboxylic acid methyl ester as yellow oil.

Workup

  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

Sources & evidence

ORD record
ord-6f469152b1c34017b846aa3d33c74870
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709509B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes