Potassium Carbonate → Methyl 5-[(3-chlorophenyl)methyl]-4-{2-[(1,1-dimethylethyl)dimethylsilyl]oxyethoxy}thiophene-3-carboxylate

HRID 1835169Notes

Reaction equation

HRID 1835169 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]2[S:13][CH:12]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[C:10]=2[OH:18])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>CC(C)=O>[CH3:7][CH2:2][CH2:3][CH:4]([CH3:8])[CH3:5].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]2[S:13][CH:12]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[C:10]=2[O:18][CH2:26][CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 23503256HCID 23503256, compound

Product 2

HCID 78922-MethylpentaneHCID 23503266Methyl 5-[(3-chlorophenyl)methyl]-4-{2-[(1,1-dimethylethyl)dimethylsilyl]oxyethoxy}thiophene-3-carboxylateYield 93.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 5-[(3chlorophenyl)methyl]-4-hydroxythiophene-3-carboxylate (11 g), potassium carbonate (5.45 g) and (2-bromoethoxy)(1,1-dimethylethyl)dimethylsilane (10 g) was dissolved in acetone (250 m) and heated at reflux for 36 hours and then allowed to cool. The mixture was filtered, concentrated and purified by chromatography, eluting with 10:1 ethyl acetate:isohexane, to give the sub-title compound (8 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 36 hours
  3. temperatureto cool
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated
  6. custompurified by chromatography
  7. washeluting with 10:1 ethyl acetate

Sources & evidence

ORD record
ord-fae5f11be5134bd484ec5ff55e8431ae
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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