Cyclopentadiene → 2,2-Bis(cyclopentadienyl)-5-trimethylsiloxypentane

HRID 1862076

反応式

HRID 1862076 の反応式
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.C[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:17][Si:18]([CH3:27])([CH3:26])[O:19][CH2:20][CH2:21][CH2:22][C:23](=O)[CH3:24]>C1COCC1>[CH:2]1([C:23]([CH:13]2[CH:12]=[CH:16][CH:15]=[CH:14]2)([CH2:22][CH2:21][CH2:20][O:19][Si:18]([CH3:27])([CH3:26])[CH3:17])[CH3:24])[CH:1]=[CH:5][CH:4]=[CH:3]1

参加物

6

反応物 4

HCID 7612CyclopentadieneHCID 8058HexaneHCID 136099385-Trimethylsiloxypentan-2-oneHCID 178418339Butyllithium

生成物 1

HCID 120953572,2-Bis(cyclopentadienyl)-5-trimethylsiloxypentane収率 17%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
65 °C

実験手順

Freshly distilled cyclopentadiene (61.5 g, 0.93 mol) was placed in a one liter Schlenk flask and dissolved in dry THF (500 ml). n-BuLi 2.5 M in hexane (372 ml 0.93 mol) was slowly added to this solution at −78° C., yielding a white precipitate. The suspension was left to reach room temperature and then heated to 65° C. for one hour. The reaction mixture is thermostated at 20° C. and a solution of 5-trimethylsiloxypentan-2-one (72.5 g, 0.42 mol) in THF (100 ml) was slowly added. The yellow suspension obtained was heated at reflux for 16 h. The resulting brown suspension was filtered and the solid washed with hexane several times. Solvents were removed under vacuum and the orange oil obtained was distilled at 10−3 mbar and 84-89° C., obtaining a yellow oil (20.5 g, 17% yield). 1H NMR (CDCl3): Λ6.40-6.02 (C5H5, 6H), 3.55 (CH2, m, 2H), 2.97, 2.80 and 2.78 (C5H5, 4H), 1.82 (CH2, m, 2H), 1.42 (CH2, m, 2H), 1.40 (CH3, s, 3H), 0.10 ((CH3)3, s, 9H).

後処理

  1. customyielding a white precipitate
  2. waitThe suspension was left
  3. customto reach room temperature
  4. customat 20° C.
  5. customThe yellow suspension obtained
  6. temperaturewas heated
  7. temperatureat reflux for 16 h
  8. filtrationThe resulting brown suspension was filtered
  9. washthe solid washed with hexane several times
  10. customSolvents were removed under vacuum
  11. customthe orange oil obtained
  12. distillationwas distilled at 10−3 mbar and 84-89° C.

出典と根拠

ORDレコード
ord-a89e9e117bfc42e8a695d3824d2b425b
出典データセット
uspto-grants-2003_03
特許番号
US06534665B1

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