1,1-Dibromoethane → 1,2-Bis(2-methyl-4-phenylindenyl)ethane

HRID 356839ノート

反応式

HRID 356839 の反応式
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][C:7]1[CH2:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Br[CH:23](Br)[CH3:24]>C1(C)C=CC=CC=1.C1COCC1>[CH3:4][C:3]1[CH:21]([CH2:23][CH2:24][CH:15]2[C:14]3[C:9](=[C:10]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:11]=[CH:12][CH:13]=3)[CH:8]=[C:7]2[CH3:6])[C:20]2[C:1]([CH:2]=1)=[C:16]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:9]=1)[CH:17]=[CH:18][CH:19]=2

参加物

6

反応物 3

HCID 112011,1-DibromoethaneHCID 42924022-Methyl-7-phenylindeneHCID 178418339Butyllithium

生成物 1

HCID 229949181,2-Bis(2-methyl-4-phenylindenyl)ethane収率 5%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

90 cm3 (0.24 mol) of a 20 % strength solution of butyl-lithium in toluene were added at room temperature under argon to a solution of 50 g (0.24 mol) of 3 in 500 ml of THF. The mixture was stirred at 60° C. for 2 hours, and cooled to -78° C., 22.5 g (0.12 mol) of dibromoethane were added, and the mixture was warmed to room temperature over the course of 18 hours. The reaction mixture was washed with 50 cm3 of H2O, the solvent was removed in vacuo, and the residue was chromatographed on 500 g of silica gel (hexane/methylene chloride 9:1), giving 2.5 g (5%) of 32 as a yellow oil which solidified slowly at -20° C.

後処理

  1. temperaturecooled to -78° C.
  2. temperaturethe mixture was warmed to room temperature over the course of 18 hours
  3. washThe reaction mixture was washed with 50 cm3 of H2O
  4. customthe solvent was removed in vacuo
  5. customthe residue was chromatographed on 500 g of silica gel (hexane/methylene chloride 9:1)

出典と根拠

ORDレコード
ord-0c3bb6c53b7a4af7af0de8fa1576f129
出典データセット
uspto-grants-1998_11
特許番号
US05840644

反応ノート

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