Potassium Carbonate → Ethyl 4-(4-(adamantan-1-yl)phenoxy)butanoate

HRID 629529Notes

Reaction equation

HRID 629529 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[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C)C=O.C(OCC)(=O)C>[C:1]12([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[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 76300Ethyl 4-bromobutyrateHCID 2699334-(1-Adamantyl)phenol

Product 1

HCID 54179703Ethyl 4-(4-(adamantan-1-yl)phenoxy)butanoateYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(adamantan-1-yl)phenol (2.0 g, 8.76 mmol) in N,N-dimethylformamide was added potassium carbonate (3.63 g, 26.29 mmol) and ethyl 4-bromobutanoate (1.29 g, 10.51 mmol), and stirred at room temperature overnight. 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 ethyl 4-(4-(adamantan-1-yl)phenoxy)butanoate as a white solid (2.7 g, 90% 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-d4c7a78401cf446384ea4e8323d7e9e2
Source dataset
uspto-grants-2016_04
Patent number
US09315507B2

Reaction notes

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