Ethyl bromoacetate → [2-(1-Hydroxy-2-methyl-propyl)-5-methoxy-4-methyl-phenoxy]-acetic acid ethyl ester

HRID 493210Notes

Reaction equation

HRID 493210 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([O:13][CH3:14])=[CH:8][C:7]=1[OH:15])[CH:3]([CH3:5])[CH3:4].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(#N)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][O:15][C:7]1[CH:8]=[C:9]([O:13][CH3:14])[C:10]([CH3:12])=[CH:11][C:6]=1[CH:2]([OH:1])[CH:3]([CH3:5])[CH3:4])[CH3:28]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 687253722-(1-Hydroxy-2-methyl-propyl)-5-methoxy-4-methyl-phenol

Product 1

HCID 68878744[2-(1-Hydroxy-2-methyl-propyl)-5-methoxy-4-methyl-phenoxy]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the above prepared 2-(1-hydroxy-2-methyl-propyl)-5-methoxy-4-methyl-phenol (2.45 g, 11.65 mmol) in 22 mL acetonitrile were successively added Cs2CO3 (4.56 g, 1.2 eq.) and ethyl bromoacetate (1.35 mL, 1.05 eq.) and the mixture vigorously stirred at ambient temperature for 3 h. Pouring onto crashed ice/NH4Cl, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=8/2), gave 3.34 g of the title compound as colorless oil.

Workup

  1. additionPouring
  2. extractionice/NH4Cl, twofold extraction with AcOEt
  3. washwashing with water and brine
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-b991bbcc886142789850468183843fd5
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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