Sodium Carbonate → HCID 86613480, 화합물

HRID 479365

반응식

HRID 479365 반응식
[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

참가 물질

5

반응물 4

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 579787Methyl 3,5-dihydroxyphenylacetateHCID 121374381-bromo-2-triisopropylsilyloxy-ethane

생성물 1

HCID 86613480HCID 86613480, 화합물

실험 절차

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]+

후처리

  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

출처 및 근거

ORD 기록
ord-5ce7fd47697248e38501b0af4c56360e
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645970B2

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