Potassium Carbonate → HCID 68813225, compound

HRID 2106427Notes

Reaction equation

HRID 2106427 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([CH2:24][CH3:25])(C3C=CC(O)=C(C)C=3)[CH2:14][CH3:15])=[CH: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:35]([O-:38])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:26]=[CH:9][C:8]2[O:12][C:11]([CH:13]([CH:14]([C:5]3[CH:6]=[CH:7][C:35]([O:38][CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[C:9]([CH3:8])[CH:26]=3)[CH3:15])[CH2:24][CH3:25])=[CH:10][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 57810551HCID 57810551, compound

Product 1

HCID 68813225HCID 68813225, compoundYield 179.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-benzofuran-5-carboxylic acid methyl ester (4.25 g, 12.1 mmol) and 1-bromopinacolone (2.70 g, 15.1 mmol) in acetone (80 mL) is treated with K2CO3 (3.33 g, 24.1 mmol) and stirred at RT for 18 h. The solid is filtered and the filtrate is concentrated, the residue is purified on column chromatography with 10-15% EtOAc/Hexane to provide the title compound (4.90 g, 90%).

Workup

  1. filtrationThe solid is filtered
  2. concentrationthe filtrate is concentrated
  3. customthe residue is purified on column chromatography with 10-15% EtOAc/Hexane

Sources & evidence

ORD record
ord-192780d6dd5f44cab472502c3d1000a6
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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