Acetone → HCID 118656069, compound

HRID 591512Notes

Reaction equation

HRID 591512 reaction equation
[C:1]([O:7][C:8]1[CH:21]=[C:20]([CH:22]=[O:23])[C:11]2[C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:13][S:14][C:10]=2[CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].CC(C)=[O:26].[O-][Mn](=O)(=O)=O.[K+]>O>[CH3:3][C:2]([CH3:4])([CH3:5])[C:1]([O:7][C:8]1[CH:9]=[C:10]2[S:14][CH:13]=[C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:11]2=[C:20]([C:22]([OH:26])=[O:23])[CH:21]=1)=[O:6]

Participants

5

Reactant 3

HCID 180AcetoneHCID 516875Potassium PermanganateHCID 89767744HCID 89767744, compound

Product 1

HCID 118656069HCID 118656069, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 4-formyl-3-(2-methoxy-2-oxoethyl)-1-benzothiophen-6-yl pivalate (150 mg), acetone (1 mL) and water (1 mL) was added KMnO4 (85 mg, 0.54 mmol) 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 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 (145 mg).

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-32724c30c51e4c7da4ec842eaa686544
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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