1,2-Dibromoethane → 1H-Indene, 3,3'-(1,2-ethanediyl)bis[4,7-dimethyl-

HRID 865317

反応式

HRID 865317 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2.[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].C[C:18]1[CH:26]=[CH:25][C:24](C)=[C:23]2[C:19]=1[CH:20]=[CH:21][CH:22]2[Li].BrCCBr>O1CCCC1.O>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[C:4]([CH2:15][CH2:14][C:13]1[C:12]3[C:20](=[C:19]([CH3:23])[CH:18]=[CH:26][C:25]=3[CH3:24])[CH2:21][CH:22]=1)=[CH:5][CH2:6]2

参加物

7

反応物 4

HCID 78391,2-DibromoethaneHCID 814584,7-dimethyl-1H-indeneHCID 178418339ButyllithiumHCID 178506817HCID 178506817、化合物

生成物 1

HCID 108599901H-Indene, 3,3'-(1,2-ethanediyl)bis[4,7-dimethyl-収率 48%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

38.2 g (265 mmol) of 4,7-dimethylindene was dissolved in 350 ml of tetrahydrofuran and the solution was cooled to 0° C. Then 165 ml of n-butyllithium (1,6M in hexane, 264 mmol) was added dropwise over 2.5 hours. After warming to room temperature and stirring for 4 hours a purple solution of 4,7-dimethylindenyl-lithium was obtained. This solution was cooled to -70° C. and treated dropwise with 25,3 g of 1,2-dibromoethane (135 mmol) in 15 ml of tetrahydrofuran over 35 min. After warming to room temperature, a pale yellow solution was obtained, and then water was added. The organic phase was collected and dried over Na2SO4. The solvent was removed by vacuum evaporation to provide 20 g of crude product (48% yield).

後処理

  1. temperatureAfter warming to room temperature
  2. customwas obtained
  3. temperatureThis solution was cooled to -70° C.
  4. temperatureAfter warming to room temperature
  5. customa pale yellow solution was obtained
  6. customThe organic phase was collected
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed by vacuum evaporation

出典と根拠

ORDレコード
ord-d661a9859bd947ce97004226853d618c
出典データセット
uspto-grants-1996_10
特許番号
US05565533

関連ノート

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