Potassium Carbonate → HCID 67086791, compound

HRID 1665174Notes

Reaction equation

HRID 1665174 reaction equation
C(OC(=O)[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[CH3:8])(C)(C)C.[C:17](=[O:20])([O-])[O-:18].[K+].[K+].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>CN(C=O)C.CCOC(C)=O>[C:9]([O:18][C:17](=[O:20])[CH2:8][CH2:7][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:13][CH:14]=1)([CH3:14])([CH3:10])[CH3:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 11322012HCID 11322012, compound

Product 1

HCID 67086791HCID 67086791, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of -(4-Hydroxy-phenyl)-propionic acid tert-butyl ester (1 g, 4.50 mmol) in dry DMF (20 ml) at room temperature under argon is added potassium carbonate (0.62 g, 4.50 mmol) followed by methyl bromoacetate (0.43 ml, 4.50 mmol) and the reaction mixture is stirred at room temperature. The reaction mixture is diluted with EtOAc and washed with water, dried (MgSO4) and evaporated in vacuo to yield a clear colourless liquid. Purification on a Waters 3000 prep HPLC system (C18, MeCN/water) yields 3-(4-Methoxycarbonylmethoxy-phenyl)-propionic acid tert-butyl ester as a pale yellow oil.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customto yield a clear colourless liquid
  5. customPurification on a Waters 3000 prep HPLC system (C18, MeCN/water)

Sources & evidence

ORD record
ord-6d56220ded6144448c021c28c162fad5
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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