Hydrochloric Acid → 1,2-bis(4,7-Dimethylindenyl)butane

HRID 1464351

反応式

HRID 1464351 の反応式
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][C:7]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]2[C:8]=1[CH:9]=[CH:10][CH2:11]2.Br[CH2:18][CH:19](Br)[CH2:20][CH3:21].Cl>CCCCCC.O1CCCC1>[CH3:4][C:3]1[CH:6]=[CH:7][C:8]([CH3:9])=[C:1]2[C:2]=1[CH:21]=[CH:20][CH:19]2[CH2:18][CH:10]([CH:11]1[C:12]2[C:8](=[C:7]([CH3:6])[CH:15]=[CH:14][C:13]=2[CH3:16])[CH:9]=[CH:10]1)[CH2:11][CH3:12]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 107921,2-DibromobutaneHCID 814584,7-dimethyl-1H-indeneHCID 178418339Butyllithium

生成物 1

HCID 190879061,2-bis(4,7-Dimethylindenyl)butane収率 10%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
60 °C

実験手順

52 ml (83.2 mmol) of a 1.6 M solution of butyllithium in hexane were added dropwise to 11.8 g (92 mmol) of 4,7-dimethylindene in 200 ml of tetrahydrofuran at room temperature under an Ar atmosphere, and the mixture was stirred at 60° C. for 1 hour. It was cooled to -78° C., 5 ml (40 mmol) of 1,2-dibromobutane were added, and stirring was continued overnight at room temperature. The reaction mixture was poured onto 2 N aqueous HCl and the organic phase was separated off, washed with saturated aqueous NaHCO3 solution and NaCl solution in succession and dried (MgSO4). The oil which remained after the solvent had been stripped off under reduced pressure was chromatographed on 350 g of silica gel (hexane). After drying under an oilpump vacuum, 1.4 g (10%) of product were obtained.

後処理

  1. temperatureIt was cooled to -78° C.
  2. stirringstirring
  3. waitwas continued overnight at room temperature
  4. customthe organic phase was separated off
  5. washwashed with saturated aqueous NaHCO3 solution and NaCl solution in succession
  6. dry with materialdried (MgSO4)
  7. customwas chromatographed on 350 g of silica gel (hexane)
  8. customAfter drying under an oilpump vacuum

出典と根拠

ORDレコード
ord-2702988df2984e0d8647bcb9044cc887
出典データセット
uspto-grants-1994_04
特許番号
US05304614

関連ノート

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