Dimethylformamide → Methyl 4-((3-methoxy-5-(trifluoromethyl)phenyl)sulfanyl)-3-oxobutanoate

HRID 591436Notes

Reaction equation

HRID 591436 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:13])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CN(C=O)C.Cl[CH2:20][C:21](=[O:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24].C([O-])([O-])=O.[K+].[K+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:13][CH2:20][C:21](=[O:27])[CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 36240Methyl 4-chloroacetoacetateHCID 221711843-Methoxy-5-(trifluoromethyl)benzenethiol

Product 1

HCID 89768260Methyl 4-((3-methoxy-5-(trifluoromethyl)phenyl)sulfanyl)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-methoxy-5-(trifluoromethyl)benzenethiol (1.36 g) and DMF (dry) (10 mL) were added methyl 4-chloroacetoacetate (1.146 mL) and K2CO3 (1.806 g) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with 1N HCl and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (1.120 g).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with 1N HCl and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-df3ecb08fd6a4c6aa9e99883f960f892
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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