Sodium Carbonate → [3-(2-Triisopropylsilyloxy-ethoxy)-5-hydroxy-phenyl]-acetic acid methyl ester

HRID 506871

Reaction equation

HRID 506871 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([OH:12])[CH:6]=1.Br[CH2:15][CH2:16][O:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([O:12][CH2:15][CH2:16][O:17][Si:18]([CH:22]([CH3:23])[CH3:24])([CH:19]([CH3:21])[CH3:20])[CH:25]([CH3:26])[CH3:27])[CH:6]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 579787Methyl 3,5-dihydroxyphenylacetateHCID 12137438Silane, (2-bromoethoxy)tris(1-methylethyl)-

Product 1

HCID 86613480[3-(2-Triisopropylsilyloxy-ethoxy)-5-hydroxy-phenyl]-acetic acid methyl ester

Procedure

A mixture of 9.39 g (51.5 mmol) of (3,5-dihydroxy-phenyl)-acetic acid methyl ester (prepared according to U. Eder, G. Sauer, G. Haffer, G. Neef, R. Wiechert, U.S. Pat. No. 4,066,674), 11.38 g (61.8 mmol) of 1-bromo-2-triisopropylsilyloxy-ethane and 14.50 g (51.5 mmol) of cesium carbonate is stirred at RT for 1 hour and at 60° C. for another hour. The reaction mixture is then treated with saturated aqueous sodium carbonate and extracted with ethyl acetate. The layers are separated and the organic layer is washed three times with saturated aqueous sodium carbonate. The aqueous layers are combined and extracted three times with ethyl acetate. The combined organic solutions are then washed with saturated brine, dried, filtered and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (85:15 hexane/ethyl acetate then 70:30 hexane/ethyl acetate and finally pure ethyl acetate) to afford above title compound as a yellow oil.

Workup

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. customThe layers are separated
  4. washthe organic layer is washed three times with saturated aqueous sodium carbonate
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic solutions are then washed with saturated brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by column chromatography on silica gel (85:15 hexane/ethyl acetate

Sources & evidence

ORD record
ord-a2d3c18a76f343ae9007e6cddc6daeb8
Source dataset
uspto-grants-2010_08
Patent number
US07786123B2

Linked notes

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