Aniline → HCID 86667941, compound

HRID 1261557Notes

Reaction equation

HRID 1261557 reaction equation
[H-].[Na+].NC1C=CC=CC=1.[CH3:10][C:11]1[CH2:15][C:14]([CH3:16])=[C:13]([CH3:17])[C:12]=1[CH3:18].Cl[Si:20]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[C:33]1([Si:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:15]2[CH:14]([CH3:16])[C:13]([CH3:17])=[C:12]([CH3:18])[C:11]=2[CH3:10])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

9

Reactant 6

HCID 6115AnilineHCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 10340Sodium CarbonateHCID 24758Sodium hydride2×HCID 1381631,2,3,4-TetramethylcyclopentadieneHCID 516892Sodium Bicarbonate

Product 1

HCID 86667941HCID 86667941, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Under nitrogen atmosphere, sodium hydride dispersed in mineral oil (0.54 g, 22.32 mmol as sodium hydride) was washed with hexane to remove mineral oil, and thereafter tetrahydrofuran (35 ml) was added. The temperature of the mixture was elevated to 50° C. and aniline (0.14 g, 1.49 mmol) was added. The mixture was stirred at 50° C. for 1 hour. A solution obtained by dissolving 1,2,3,4-tetramethylcyclopenta-1,3-diene (2.00 g, 16.37 mmol) in tetrahydrofuran (9 ml) was added dropwise to this, and the mixture was stirred at 50° C. for 2 hours and cooled to 20° C. To the solution, a solution obtained by dissolving chlorotriphenylsilane (4.39 g, 14.88 mmol) in toluene (9 ml) was added dropwise, and the mixture was stirred at 35° C. overnight. The resultant mixture was added dropwise at 0° C. to a mixture of a 10% sodium hydrogen carbonate solution (22 ml) and a 10% sodium carbonate solution (22 ml). Toluene (22 ml) was added to separate an organic phase. The organic phase was dried over sodium sulfate and filtrated, and the solvent was concentrated under reduced pressure to obtain 1-triphenylsilyl-2,3,4,5-tetramethylcyclopentadiene (3.76 g, yield 66.3%).

Workup

  1. washwas washed with hexane
  2. customto remove mineral oil
  3. additiontetrahydrofuran (35 ml) was added
  4. customwas elevated to 50° C.
  5. customA solution obtained
  6. additionwas added dropwise to this, and the mixture
  7. stirringwas stirred at 50° C. for 2 hours
  8. temperaturecooled to 20° C
  9. customTo the solution, a solution obtained
  10. additionwas added dropwise
  11. stirringthe mixture was stirred at 35° C. overnight
  12. customto separate an organic phase
  13. dry with materialThe organic phase was dried over sodium sulfate
  14. filtrationfiltrated
  15. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4a27b426ef3e4feb99800d68c4f81462
Source dataset
uspto-grants-2013_06
Patent number
US08470947B2

Reaction notes

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