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 1636211Notes

Reaction equation

HRID 1636211 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-a954396b350546fba2a96646bffeca25
Source dataset
uspto-grants-2000_03
Patent number
US06034022

Reaction notes

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