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Water → 3-{[2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-2-methylphenol

HRID 1067134
ノート
印刷プレビュー

反応式

HRID 1067134 の反応式
C[O:2][C:3]1[C:4]([CH3:33])=[C:5]([CH:30]=[CH:31][CH:32]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH:9]=[C:8]1[C:13]1[O:14][C:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:17]=1.B(Br)(Br)Br.O>C(Cl)Cl>[C:18]1([C:16]2[N:17]=[C:13]([C:8]3[CH:7]([CH2:6][C:5]4[C:4]([CH3:33])=[C:3]([OH:2])[CH:32]=[CH:31][CH:30]=4)[CH2:12][CH2:11][CH2:10][CH:9]=3)[O:14][C:15]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 25134Boron tribromideHCID 183673122-[1-(3-Methoxy-2-methylbenzyl)-2-cyclohexen-2-yl]-4,5-diphenyloxazole

生成物 1

HCID 183674223-{[2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-2-methylphenol収率 80.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

To a solution of 2-[1-(3-methoxy-2-methylbenzyl)-2-cyclohexen-2-yl]-4,5-diphenyloxazole (1.16 g) in CH2Cl2 (25 ml) was added boron tribromide (1M solution in CH2Cl2, 5.32 ml) at −60° C. and the mixture was warmed to 5° C. After stirring for 1 hour at the same temperature, the reaction mixture was stirred for further 1 hour at room temperature. To the mixture was added water under ice-cooling, extracted with EtOAc. The organic layer was washed with water, saturated sodium hydrogen carbonate, water, and brine, dried over magnesium sulfate, evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 5:1) to give 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-2-methylphenol (903.8 mg) as an amorphous solid.

後処理

  1. stirringthe reaction mixture was stirred for further 1 hour at room temperature
  2. temperaturecooling
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water, saturated sodium hydrogen carbonate, water, and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 5:1)

出典と根拠

ORDレコード
ord-dccc98888f3d4257b7b2609004fae252
出典データセット
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06245790B1

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート