Phenol → HCID 9909232、化合物

HRID 1637200ノート

反応式

HRID 1637200 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:11]1[C:12]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:21][C:13]=2[S:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C)C=O>[O:7]([C:11]1[C:12]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:21][C:13]=2[S:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 11046271HCID 11046271、化合物

生成物 1

HCID 9909232HCID 9909232、化合物収率 17%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

Phenol (108 mg, 1.15 mmol) was added to a stirred suspension of sodium hydride (46 mg of 60% dispersion in mineral oil, 1.15 mmol) in anhydrous dimethylformamide (1 ml), under a nitrogen atmosphere. Ethyl 3-chloro-6-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylate (Preparation 4, 200 mg, 0.58 mmol) was added to the mixture after 30 minutes, and the mixture was then heated to 75° C. for 48 hours. The reaction was partitioned between ethyl acetate and water. The organics were separated and washed with water, dried (magnesium sulfate) and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using diethyl ether as eluant. The isolated product was crystallised from hexane to give the title compound as a colourless solid (40 mg).

後処理

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe organics were separated
  3. washwashed with water
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customchromatographed on silica gel
  7. customThe isolated product was crystallised from hexane

出典と根拠

ORDレコード
ord-184108eb7b4e4b9dbc1139184ebfd988
出典データセット
uspto-grants-2000_03
特許番号
US06040309

反応ノート

読み込み中…