Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silane → N-tert-Butyl-1,1-dimethyl-1-(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silanamine

HRID 881777Notes

Reaction equation

HRID 881777 reaction equation
Cl[Si:2]([CH3:13])([CH3:12])[CH:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([CH3:10])=[C:4]1[CH3:11].[C:14]([NH-:18])([CH3:17])([CH3:16])[CH3:15].[Li+]>O1CCCC1>[C:14]([NH:18][Si:2]([CH:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([CH3:10])=[C:4]1[CH3:11])([CH3:13])[CH3:12])([CH3:17])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 5045335Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silaneHCID 10964401Lithium t-butylamide

Product 1

HCID 3533593N-tert-Butyl-1,1-dimethyl-1-(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silanamineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3,4,5-tetramethylcyclopenta-2,4-diene (3.67 g, 30 mmol) was added into a flask containing tetrahydrofuran (100 mL), n-butyl lithium (12 mL) was added in droplets thereto at 0° C., and the reaction temperature was gradually increased to room temperature so that the reaction was carried out for 8 hours. This solution was cooled to −78° C., dichloromethylsilane (3.87g, 30 mmol) was slowly added in droplets thereto, and then the reaction was carried out for 12 hours. After the reaction, the volatile material was removed, and the resultant product was extracted with hexane (100 mL), after which the volatile material was removed, thereby obtaining as pale yellow oil 5.5 g of (chloro) (dimethyl) (2,3,4,5-tetramethylcyclopentadienyl)silane. The (chloro)(dimethyl)(2,3,4,5-tetramethylcyclopentadienyl)silane thus obtained was dissolved in tetrahydrofuran (100 mL) without additional purification, after which lithium tert-butylamide (2.02 g) was added in droplets thereto at 0° C. and the reaction was carried out at room temperature for 2 hours. After the reaction, the volatile material was removed, and the resultant product was extracted with hexane (100 mL), thus obtaining as pale yellow oil 6.09 g (yield 81%) of (tert-butylamino) (2,3,4,5-tetramethylcyclopenta-2,4-dienyl)dimethylsilane.

Workup

  1. customAfter the reaction
  2. customthe volatile material was removed
  3. extractionthe resultant product was extracted with hexane (100 mL)

Sources & evidence

ORD record
ord-c7a22d00e236422cb60311092c0efb02
Source dataset
uspto-grants-2015_03
Patent number
US08993694B2

Reaction notes

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