HCID 89768162, compound → HCID 121223266, compound

HRID 591411Notes

Reaction equation

HRID 591411 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:5]=[C:6]([OH:8])[CH:7]=1>S(O)(C)(=O)=O>[CH3:16][O:15][C:13](=[O:14])[CH2:12][C:11]1[C:5]2[C:6]([OH:8])=[CH:7][C:2]([OH:1])=[CH:3][C:4]=2[S:9][CH:10]=1

Participants

3

Reactant 1

HCID 89768162HCID 89768162, compound

Product 1

HCID 121223266HCID 121223266, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

To MsOH (50 mL) was added methyl 4-((3,5-dihydroxyphenyl)sulfanyl)-3-oxobutanoate (15.1 g) at room temperature. The mixture was stirred at room temperature for 30 min. The mixture was poured into ice-water at 0° C. 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). The product was crystallized from EtOAc-IPE to give the title compound (7.20 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)
  7. customThe product was crystallized from EtOAc-IPE

Sources & evidence

ORD record
ord-faa6c934c3b44bcfbcde5a324c9c93f5
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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