Dimethylformamide → Methyl 4-((2-fluoro-3-methoxy-5-methylphenyl)sulfanyl)-3-oxobutanoate

HRID 591444Notes

Reaction equation

HRID 591444 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH3:10])=[CH:4][C:3]=1[SH:11].CN(C=O)C.C([O-])([O-])=O.[K+].[K+].Cl[CH2:24][C:25](=[O:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28]>O>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH3:10])=[CH:4][C:3]=1[S:11][CH2:24][C:25](=[O:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 36240Methyl 4-chloroacetoacetateHCID 897676722-Fluoro-3-methoxy-5-methylbenzenethiol

Product 1

HCID 89767691Methyl 4-((2-fluoro-3-methoxy-5-methylphenyl)sulfanyl)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-fluoro-3-methoxy-5-methylbenzenethiol (289.4 mg) and DMF (dry) (12 mL) were added K2CO3 (255 mg) and methyl 4-chloro-3-oxobutanoate (0.217 mL) at 0° C. The mixture was stirred at room temperature for 1.5 h. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed successively with water 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 (330 mg).

Workup

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

Sources & evidence

ORD record
ord-2d2e73a62ef9416c9beb5543f0b261a6
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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