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

HRID 1862076

반응식

HRID 1862076 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
65 °C

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-a89e9e117bfc42e8a695d3824d2b425b
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534665B1

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