Trismethoxyresveratrol → 5-(2-(4-Hydroxyphenyl)Ethenyl)Benzene-1,3-Diol

HRID 1411223

反応式

HRID 1411223 の反応式
C[O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)[CH:6]=[C:7]([O:9]C)[CH:8]=1.Cl.N1C=CC=CC=1>CC(O)=O>[C:5]1([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:6]=[C:7]([OH:9])[CH:8]=[C:3]([OH:2])[CH:4]=1

参加物

4

反応物 2

HCID 5388063TrismethoxyresveratrolHCID 10176127Pyridinium chloride

生成物 1

HCID 50565-(2-(4-Hydroxyphenyl)Ethenyl)Benzene-1,3-Diol

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
90 °C

実験手順

To a 250 mL round-bottomed flask equipped with a magnetic stir bar was added 8 (2.7 g, 10 mmol) and pyridine hydrochloride (10.4 g, 90 mmol, 9 equiv). A reflux condenser was equipped and the reaction mixture was refluxed for 2 h under an N2 atmosphere. Afterwards, the mixture was allowed to cool to ˜90° C. and quenched into H2O (200 mL) whereupon a purplish colored solid precipitated. The mixture was extracted with EtOAc (50 mL×3). The extracts were collected and diluted with hexanes (100 mL) and then filtered through a thin pad of silica gel to remove dark colored, polar impurities. The filtrate was evaporated in vacuo leaving an off-white solid. The crude product was slurried with HOAc and filtered to give resveratrol as a tan microcrystalline powder (450 mg, 20%), mp. 258-261° C., lit. 261° C. 1H NMR (DMSO): δ 9.59 (s, OH), 9.23 (s, 20H), 7.41 (d, J=8.9 Hz, 2H), 6.95 (d, Jab=16.3 Hz, 1H), 6.82 (d, Jab=16.3 Hz, 1H), 6.76 (d, J=8.9 Hz, 2H), 6.39 (d, J=2.0 Hz, 2H), 6.13 (t, J=2.1 Hz, 1H); 13C NMR (DMSO): δ 158.58, 157.28, 139.36, 128.15, 127.96, 127.92, 125.74, 115.61, 104.41, 101.87. Anal. Calcd for C14H12O3: C, 73.67; H, 5.30. Found: C, 73.40; H, 5.44.

後処理

  1. customTo a 250 mL round-bottomed flask equipped with a magnetic stir bar
  2. customA reflux condenser was equipped
  3. temperaturethe reaction mixture was refluxed for 2 h under an N2 atmosphere
  4. customquenched into H2O (200 mL) whereupon a purplish colored solid
  5. customprecipitated
  6. extractionThe mixture was extracted with EtOAc (50 mL×3)
  7. customThe extracts were collected
  8. additiondiluted with hexanes (100 mL)
  9. filtrationfiltered through a thin pad of silica gel
  10. customto remove dark colored
  11. customThe filtrate was evaporated in vacuo
  12. customleaving an off-white solid
  13. filtrationfiltered

出典と根拠

ORDレコード
ord-fb090d7d0db84de7b796fcb36b28e731
出典データセット
uspto-grants-2014_12
特許番号
US08921614B1

関連ノート

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