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

HRID 479365

反応式

HRID 479365 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

実験手順

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]+

後処理

  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

出典と根拠

ORDレコード
ord-5ce7fd47697248e38501b0af4c56360e
出典データセット
uspto-grants-2003_11
特許番号
US06645970B2

関連ノート

読み込み中…