Methanol → HCID 131734525, compound

HRID 591514Notes

Reaction equation

HRID 591514 reaction equation
C([O:7][C:8]1[CH:21]=[C:20]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[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)C(C)(C)C.CO.C([O-])([O-])=O.[K+].[K+]>O>[CH3:19][O:18][C:16](=[O:17])[CH2:15][C:12]1[C:11]2[C:20]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])=[CH:21][C:8]([OH:7])=[CH:9][C:10]=2[S:14][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 89767712HCID 89767712, compound

Product 1

HCID 131734525HCID 131734525, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-(dimethylcarbamoyl)-3-(2-methoxy-2-oxoethyl)-1-benzothiophen-6-yl pivalate (128 mg) and MeOH (3 mL) was added K2CO3 (46.9 mg) at room temperature. The mixture was stirred at room temperature for 12 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (75 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with 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-d36da992e3f6425189333dc693bb1aaf
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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