Potassium Carbonate → HCID 57871409, compound

HRID 550218Notes

Reaction equation

HRID 550218 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([CH2:26][CH3:27])([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH3:25])[CH:19]=3)[CH2:16][CH3:17])=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].Br[CH2:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[C:20]([CH3:25])[CH:19]=3)([CH2:26][CH3:27])[CH2:16][CH3:17])=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 57871398HCID 57871398, compound

Product 1

HCID 57871409HCID 57871409, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Stir a mixture of 7-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester (0.87 g, 2.40 mmol), 1-bromopinacolone (1.54 g, 8.68 mmol), and potassium carbonate (2.4 g, 17.4 mmol) in acetone (20 mL) for 4 h at RT. Concentrate the reaction mixture and then dilute the residue with EtOAc (100 mL) and water (50 mL). Adjust the pH of the mixture to 1 using 1 N HCl. Discard the aqueous layer. Wash the organic layer with brine, dry over Na2SO4 and filter. Concentrate the filtrate and purified by silica gel radial chromatography (5:95 EtOAc:hex to 15:85 EtoAc:hex) to give the title compound as a white solid (1.1 g, 82%). MS (ES) m/e 461 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture
  2. additiondilute the residue with EtOAc (100 mL) and water (50 mL)
  3. washWash the organic layer with brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationConcentrate the filtrate
  7. custompurified by silica gel radial chromatography (5:95 EtOAc:hex to 15:85 EtoAc:hex)

Sources & evidence

ORD record
ord-a8642cd0c17b431f86a7cb79fc08277c
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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