Potassium Carbonate → HCID 57835421, compound

HRID 730966Notes

Reaction equation

HRID 730966 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13]([CH2:24][CH3:25])([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:23])[CH:17]=3)[CH2:14][CH3:15])[S:10][C:9]=2[CH:26]=1)=[O:4].Br[CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:18]([CH3:23])[CH:17]=3)([CH2:24][CH3:25])[CH2:14][CH3:15])[S:10][C:9]=2[CH:26]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 57835419HCID 57835419, compound

Product 1

HCID 57835421HCID 57835421, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-benzo[b]thiophene-6-carboxylic acid methyl ester (4.05 g, 11.0 mmol) and 1-bromopinacolone (2.36 g, 13.2 mmol) in acetone (100 mL) is treated with K2CO3 (3.04 g, 22.0 mmol) and stirred at RT for 16 h. The mixture is filtered, and the filtrate is concentrated. The residue is purified by silica gel column chromatography (10-15% EtOAc/Hex) to provide the title compound (4.50 g, 88%).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by silica gel column chromatography (10-15% EtOAc/Hex)

Sources & evidence

ORD record
ord-785c040015c248178f90730b06793acb
Source dataset
uspto-grants-2009_09
Patent number
US07582775B2

Reaction notes

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