Sodium Carbonate → HCID 86613480, compound

HRID 479365

Reaction equation

HRID 479365 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 121374381-bromo-2-triisopropylsilyloxy-ethane

Product 1

HCID 86613480HCID 86613480, compound

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. MS (EI, negative ionization) m/z 381 [M−H]−, (EI, positive ionization) m/z 405 [M+Na]+

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-5ce7fd47697248e38501b0af4c56360e
Source dataset
uspto-grants-2003_11
Patent number
US06645970B2

Linked notes

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