Methanol → Z-3-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic acid methyl ester

HRID 2238251

反応式

HRID 2238251 の反応式
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:9]=[C:10](/[CH:16]=[C:17](/[C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)\[C:18]([OH:20])=[O:19])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1.[CH3:28]O>>[CH3:28][O:19][C:18](=[O:20])/[C:17](/[C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)=[CH:16]\[C:10]1[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=[C:8]([O:7][CH3:6])[CH:9]=1

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5386532Z-3-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)-acrylic acid

生成物 1

HCID 15541463Z-3-(3,5-Dimethoxyphenyl)-2-(4-hydroxyphenyl)acrylic acid methyl ester収率 35%

実験手順

Concentrated sulfuric acid. (10 drops) was added to a stirred methanol suspension of thoroughly dried 19 (0.60 g, 2.0 mmol) under argon and heated at reflux for 18 h. Methanol was evaporated under reduced pressure, residue was taken up in ethyl acetate (20 mL) and washed with water (20 mL), saturated aqueous Na HCO3 (10 mL) and brine (10 mL). The organic layer was dried on anhydrous magnesium sulfate, filtered and the solvent was evaporated. The crude product obtained was purified by chromatography over silica gel and eluted with hexane-ethyl acetate (7:3) to yield 20 as white solid (0.24 g, 35%): 1HNMR (400 MHz, CDCl3) δ 7.26 (d, J=8.4 Hz, 2H), 6.82 (s, 1H), 6.76 (d, J=8.4 Hz, 2H), 6.45 (d, J=2.0 Hz, 2H), 6.34 (t, J=2.0 Hz, 1H), 4.97 (s, 1H), 3.73 (s, 3H), 3.72 (s, 6H).

後処理

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. customMethanol was evaporated under reduced pressure, residue
  4. washwashed with water (20 mL), saturated aqueous Na HCO3 (10 mL) and brine (10 mL)
  5. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe crude product obtained
  9. customwas purified by chromatography over silica gel
  10. washeluted with hexane-ethyl acetate (7:3)

出典と根拠

ORDレコード
ord-f89114a8f9944711b3f33ed1c429ec32
出典データセット
uspto-grants-2010_05
特許番号
US07718682B2

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