Potassium Carbonate → HCID 57986677, compound

HRID 1615881Notes

Reaction equation

HRID 1615881 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([Cl:11])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[Si:19]([O:26][CH2:27][CH2:28]Br)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:28][CH2:27][O:26][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[C:6]([Cl:11])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 57986677HCID 57986677, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2.50 g of 3-chloro-4-hydroxybenzoic acid methyl ester in 25 ml of DMF, 2.78 g of potassium carbonate and 4.31 ml of 2-(tert-butyldimethylsilyloxy)ethylbromide were added, and the mixture was stirred at 50° C. for 15 hours. The solvent was evaporated, EtOAc was added to the residue, and the organic layer was washed with water and brine and dried over sodium sulfate. After the evaporation of the solvent, the obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=10:1˜5:1) to obtain 4.88 g of 4-[2-(tert-butyldimethylsilyloxy)ethoxy]-3-chlorobenzoic acid methyl ester.

Workup

  1. customThe solvent was evaporated
  2. additionEtOAc was added to the residue
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customAfter the evaporation of the solvent
  6. customthe obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=10:1˜5:1)

Sources & evidence

ORD record
ord-281f8e41c2754375ad93af4618fe99bd
Source dataset
uspto-grants-2014_07
Patent number
US08765764B2

Reaction notes

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