N,N-Dimethylaniline → Resveratrol

HRID 1267679

反応式

HRID 1267679 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].CN(C)C1C=CC=CC=1.C([O:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]2[CH:35]=[C:34]([O:36]CC3C=CC=CC=3)[CH:33]=[C:32]([O:44]CC3C=CC=CC=3)[CH:31]=2)=[CH:24][CH:23]=1)C1C=CC=CC=1>ClCCl>[OH:36][C:34]1[CH:35]=[C:30](/[CH:29]=[CH:28]/[C:25]2[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=2)[CH:31]=[C:32]([OH:44])[CH:33]=1

参加物

5

反応物 3

HCID 949N,N-DimethylanilineHCID 6451240Aluminum(III) ChlorideHCID 10217778(E)-3,5,4'-Tribenzyloxystilbene

生成物 1

HCID 445154Resveratrol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
45 °C

実験手順

In a 3 lit. round-bottomed flask equipped with a thermometer are added aluminum chloride (390.35 gm) and N, N-dimethylaniline (413.10 gm) maintaining the temperature at 40-50° C.(exothermic). To this solution, (E)-1-[4-(benzyloxy)phenyl]-2-[3,5-bis(benzyloxy)phenyl]ethene (243 gm) in dichloromethane (800 ml) is added and stirred for further 0.75 hour. After the reaction is over, the reaction mixture is quenched into dil. hydrochloric acid at 0-5° C. and extracted with ethyl acetate. The organic layer is charcoalized and concentrated to get pure (E)-1-(3,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)ethene (trans-Resveratrol) in the exclusive trans form. Mp 257-259° C. 1H NMR (DMSO-d6, 400 MHz) δ 6.11 (t, J=1.8 Hz, 1H), 6.38(d, J=1.8 Hz, 2H), 6.75 (d, J=8.5 Hz, 2H), 6.82(d, J=16.3 Hz, 1H), 6.92(d, J=16.3, 1H), 7.39(d, J=8.4 Hz, 2H); Mass M/e:228.2

後処理

  1. customIn a 3 lit. round-bottomed flask equipped with a thermometer
  2. customis quenched into dil. hydrochloric acid at 0-5° C.
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-1fbfab3fe1fa4d9b8bdd9c920fdc18e2
出典データセット
uspto-grants-2003_04
特許番号
US06552213B1

関連ノート

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