Dimethylformamide → Methyl 4-((3-fluoro-5-methoxyphenyl)sulfanyl)-3-oxobutanoate

HRID 591560Notes

Reaction equation

HRID 591560 reaction equation
Cl[CH2:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[F:10][C:11]1[CH:12]=[C:13]([SH:19])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1.CN(C=O)C>O>[F:10][C:11]1[CH:12]=[C:13]([S:19][CH2:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 36240Methyl 4-chloroacetoacetateHCID 897677523-Fluoro-5-methoxybenzenethiol

Product 1

HCID 89768091Methyl 4-((3-fluoro-5-methoxyphenyl)sulfanyl)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-chloroacetoacetate (1.871 mL), K2OC3 (2.210 g), 3-fluoro-5-methoxybenzenethiol (2.3 g) and DMF (30 mL) was stirred at room temperature for 1 h. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, 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 (2.87 g).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water 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-75d09aaaaa54434dad06955e30bff04f
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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