Potassium Carbonate → HCID 57871406, compound

HRID 550205Notes

Reaction equation

HRID 550205 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([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: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][CH:9]=[C:10]([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:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 57871411HCID 57871411, compound

Product 1

HCID 57871406HCID 57871406, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Stir a mixture containing 6-[1-ethyl-1-(4-hydroxy-3-methylphenyl)propyl]naphthalene-2-carboxylic acid methyl ester (0.87 g, 2.40 mmol), 1-bromopinacolone (0.64 g, 3.60 mmol), and potassium carbonate (1.0 g, 7.2 mmol) in acetone (15 mL) at RT for 16 h. Concentrate the reaction mixture and 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 and wash the organic layer with brine, dry over Na2SO4, then filter. Concentrate the filtrate and purify by silica gel radial chromatography (5:95 EtOAc:hex to 15:85 EtoAc:hex) to give the title compound as an off-white solid (0.53 g, 48%). 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. custompurify by silica gel radial chromatography (5:95 EtOAc:hex to 15:85 EtoAc:hex)

Sources & evidence

ORD record
ord-bf717e1047bb4ddfabd2ced19cdb7ebc
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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