Dimethylsilyl(t-butylamino)chloride → N-(1,1-dimethylethyl)-1,1-dimethyl-1-(1,5,6,7-tetrahydro-2-methyl-s-indacen-1-yl)silanamine

HRID 1739522Notes

Reaction equation

HRID 1739522 reaction equation
[CH3:1][C:2]1[CH:3]([Li])[C:4]2[C:12]([CH:13]=1)=[CH:11][C:10]1[CH2:9][CH2:8][CH2:7][C:6]=1[CH:5]=2.[CH3:15][SiH:16]([N:18](Cl)[C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:17]>C1COCC1>[CH3:20][C:19]([NH:18][Si:16]([CH3:17])([CH3:15])[CH:3]1[C:4]2[C:12](=[CH:11][C:10]3[CH2:9][CH2:8][CH2:7][C:6]=3[CH:5]=2)[CH:13]=[C:2]1[CH3:1])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 123286153Dimethylsilyl(t-butylamino)chlorideHCID 178506824HCID 178506824, compound

Product 1

HCID 15457415N-(1,1-dimethylethyl)-1,1-dimethyl-1-(1,5,6,7-tetrahydro-2-methyl-s-indacen-1-yl)silanamineYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1,5,6,7-tetrahydro-2-methyl-s-indacen-1-yl) lithium (25.0 g, 0.1419 moles) in THF (200 mL) was added dropwise to a solution of dimethylsilyl(t-butylamino)chloride (23.518 g, 0.1419 moles) in THF (250 mL) over a 1 hour period of time. This mixture was then allowed to stir for 20 hours. After the reaction period the volatiles were removed and the residue extracted and filtered using hexane. Removal of the hexane resulted in the isolation of the desired product as a red-yellow oil (37.55 g, 88.0 percent).

Workup

  1. customAfter the reaction period the volatiles
  2. customwere removed
  3. extractionthe residue extracted
  4. filtrationfiltered
  5. customRemoval of the hexane

Sources & evidence

ORD record
ord-eea70fe6c91844b28a9952e5c77298f3
Source dataset
uspto-grants-1999_10
Patent number
US05965756

Reaction notes

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