Potassium Carbonate → HCID 86729433, compound

HRID 629532Notes

Reaction equation

HRID 629532 reaction equation
[C:1]12([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].Br[C:25]([CH3:31])([CH3:30])[C:26]([O:28][CH3:29])=[O:27]>CN(C)C=O.C(OCC)(=O)C>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:25]([CH3:31])([CH3:30])[C:26]([O:28][CH3:29])=[O:27])=[CH:15][CH:16]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 90097Methyl 2-bromo-2-methylpropionateHCID 2699334-(1-Adamantyl)phenol

Product 1

HCID 86729433HCID 86729433, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(adamantan-1-yl)phenol (0.8 g, 3.50 mmol) in N,N-dimethylformamide (8 mL) was added anhydrous potassium carbonate (1.45 g, 10.51 mmol) and methyl 2-bromo-2-methylpropanoate (1.15 g, 7.0 mmol), and stirred at room temperature for 12 hours. The reaction mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified by silica gel column chromatography to give methyl 2-(4-(adamantan-1-yl)phenoxy)-2-methylpropanoate as colorless oil (1.1 g, 94.1% yield).

Workup

  1. washwashed with aqueous sodium bicarbonate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe solvent was filtered
  4. customevaporated under reduced pressure
  5. customto afford a crude solid, which
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e65c5b8d40d44975b0a72df4c58ec8be
Source dataset
uspto-grants-2016_04
Patent number
US09315507B2

Reaction notes

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