Ethyl Acetate → (2,3-Dihydroxy-4-methoxy-phenyl)-(1,2,3-trimethoxy-8,9-dihydro-7H-benzocyclohepten-5-yl)-methanone

HRID 33956

反応式

HRID 33956 の反応式
C([O:8][C:9]1[C:14]([O:15]CC2C=CC=CC=2)=[C:13]([O:23][CH3:24])[CH:12]=[CH:11][C:10]=1[C:25]([C:27]1[C:33]2[CH:34]=[C:35]([O:42][CH3:43])[C:36]([O:40][CH3:41])=[C:37]([O:38][CH3:39])[C:32]=2[CH2:31][CH2:30][CH2:29][CH:28]=1)=[O:26])C1C=CC=CC=1.C1CC=CCC=1.CC(=O)OCC>CCO.[Pd]>[OH:8][C:9]1[C:14]([OH:15])=[C:13]([O:23][CH3:24])[CH:12]=[CH:11][C:10]=1[C:25]([C:27]1[C:33]2[CH:34]=[C:35]([O:42][CH3:43])[C:36]([O:40][CH3:41])=[C:37]([O:38][CH3:39])[C:32]=2[CH2:31][CH2:30][CH2:29][CH:28]=1)=[O:26]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 123431,4-CyclohexadieneHCID 68920825(2,3-Bis-benzyloxy-4-methoxy-phenyl)-(1,2,3-trimethoxy-8,9-dihydro-7H-benzocyclohepten-5-yl)-methanone

生成物 1

HCID 15986323(2,3-Dihydroxy-4-methoxy-phenyl)-(1,2,3-trimethoxy-8,9-dihydro-7H-benzocyclohepten-5-yl)-methanone収率 63%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
25 °C

実験手順

95 (0.69 g, 1.19 mmol) was dissolved in 20 mL of anhydrous EtOH under nitrogen and the reaction mixture was immersed in a water bath to maintain a temperature of 25° C. 1.2 g of Pd—C was added followed by 1,4-cyclohexadiene (1.13 mL, 11.90 mmol) and the reaction mixture was stirred for 7 h. The reaction mixture was monitored for completion by TLC (Rf: 0.32, 60:40 Hex:EA). The reaction mixture was filtered through celite, washed with ethylacetate, rotavaped and purified by column chromatography (20:80 EtOAc:Hexanes) to obtain 0.3 g (63%) of 23 as yellow oil.

後処理

  1. customthe reaction mixture was immersed in a water bath
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with ethylacetate
  4. custompurified by column chromatography (20:80 EtOAc:Hexanes)

出典と根拠

ORDレコード
ord-1618bf0e6699400c86ae13927af39f95
出典データセット
uspto-grants-2008_09
特許番号
US07429681B2

関連ノート

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