4-Chloro-2-(propan-2-yl)-1H-indene → 4-(3,5-Dimethylphenyl)-2-isopropylindene

HRID 842457ノート

反応式

HRID 842457 の反応式
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH2:6]2.[CH3:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[C:19]([CH3:21])[CH:20]=1>CCOCC.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:14][C:15]1[CH:16]=[C:17]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH2:6]3)[CH:18]=[C:19]([CH3:21])[CH:20]=1

参加物

5

反応物 2

HCID 219183974-Chloro-2-(propan-2-yl)-1H-indeneHCID 178425074HCID 178425074、化合物

生成物 1

HCID 220230144-(3,5-Dimethylphenyl)-2-isopropylindene

試薬・触媒・溶媒 2

HCID 178418751HCID 178418751、化合物触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

4-chloro-2-isopropylindene (10 g, 54 mmol) and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 150 mL of Et2O. 3,5-Dimethylphenylmagnesium bromide (54 mmol) as a Et2O solution was added under vigorous stirring and the reaction was stirred overnight at room temperature. After overnight stirring, the reaction was slowly quenched with H2O to neutralize unreacted Grignard. The solution was subsequently treated with 100 mL of 10% HCl(aq), and neutralized with saturated sodium bicarbonate aqueous solution. The organic layer was dried with magnesium sulfate and the solvent was removed by rotary evaporation. The remaining residue was loaded onto a silica gel column and eluted with hexane. Yield was 5.5 g (39%).

後処理

  1. stirringthe reaction was stirred overnight at room temperature
  2. stirringAfter overnight stirring
  3. customthe reaction was slowly quenched with H2O
  4. additionThe solution was subsequently treated with 100 mL of 10% HCl(aq)
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. customthe solvent was removed by rotary evaporation
  7. washeluted with hexane

出典と根拠

ORDレコード
ord-12131979fdb446fa830cd9987b3d7730
出典データセット
uspto-grants-2002_04
特許番号
US06376413B1

反応ノート

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