HCID 89767847, compound → HCID 131734521, compound

HRID 591499Notes

Reaction equation

HRID 591499 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:18])=[C:5]([S:9][CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=1>S(O)(C)(=O)=O>[CH3:16][O:15][C:13](=[O:14])[CH2:12][C:11]1[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([CH3:18])[C:5]=2[S:9][CH:10]=1

Participants

3

Reactant 1

HCID 89767847HCID 89767847, compound

Product 1

HCID 131734521HCID 131734521, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

Methyl 4-((3-methoxy-2-methylphenyl)sulfanyl)-3-oxobutanoate (3.51 g) was added to MsOH (20 mL) at room temperature. The mixture was stirred at room temperature for 15 min. The mixture was poured into ice-water at 0° C. and extracted with EtOAc. The organic layer was separated, washed successively with 1N NaOH 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 (3.10 g).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with 1N NaOH 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-27266acbf50145bd86b612fa99d1cfd4
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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