Chlorotrimethylsilane → HCID 15319840, 화합물

HRID 1739646노트

반응식

HRID 1739646 반응식
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH:14]=2)([CH3:12])[CH3:11])=[CH:2]1.C1COCC1.[Li]CCCC.[Si:32](Cl)([CH3:35])([CH3:34])[CH3:33]>CCCCCC.O>[CH3:33][Si:32]([CH3:35])([CH3:34])[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([C:10]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:1]([Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:2]=2)([CH3:12])[CH3:11])=[CH:14]1

참가 물질

7

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 109126573,3'-(1-Methylethylidene)bis[1H-indene]HCID 178418339Butyllithium

생성물 1

HCID 15319840HCID 15319840, 화합물수율 95.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8058Hexane용매

실험 절차

3.3 g of 2,2-bis(3-indenyl)propane (20511/46, MW 272.39, 12.11 mmol) and 50 m of THF in a 100 mL flask were cooled to -70° C. while stirring. 17 mL of a 1.6 M solution of BuLi (27.2 mmol) in hexane were added dropwise. At the end of the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The solution was cooled again to -70° C. and 3.4 mL of Me3SiCl (MW 108.64, d 0.856, 26.8 mmol) were added. At the end of the addition, the reaction mixture was allowed to warm to room temperature and stirred for 2 h. Water is then added, the organic layer is separated and the water layer extracted twice with Et2O, all organic phases were combined and dried over MgSO4, then filtered and all volatiles removed in vacuo. 4.8 g (95%) of a mixture of rac/meso 2,2-bis(1-trimethylsilyl-3-indenyl)propane was obtained. 1H NMR (200 MHz, C2D2Cl4, 120° C., referenced to the peak of residual C2HDCl4 at 5.75 ppm): 7.1-7.3 (m, 4H, C6 ring), 6.75-6.95 (m, 4H, C6 ring), 6.3-6.4 (br s, 2H, C5 ring), 3.2-3.3 (m, 2H, C5 ring), 1.64, 1.62 (2 s, 6H, bridge methyls), -0.15, -0.17 (2 s, 18H, TMS methyls).

후처리

  1. additionAt the end of the addition
  2. stirringstirred for 1 h
  3. temperatureThe solution was cooled again to -70° C.
  4. additionAt the end of the addition
  5. temperatureto warm to room temperature
  6. stirringstirred for 2 h
  7. customthe organic layer is separated
  8. extractionthe water layer extracted twice with Et2O
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customall volatiles removed in vacuo

출처 및 근거

ORD 기록
ord-ab133960c4b34d1298b4af1518bb3088
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968863

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