t-Butylaminodimethylsilylchloride → HCID 17917408, compound

HRID 1387665Notes

Reaction equation

HRID 1387665 reaction equation
[CH3:1][N:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([Li])[CH:4]=1.[C:19]([NH:23][Si:24](Cl)([CH3:26])[CH3:25])([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[CH3:20][C:19]([NH:23][Si:24]([CH3:26])([CH3:25])[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([N:2]([CH3:1])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4]1)([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 11205972t-ButylaminodimethylsilylchlorideHCID 178506842HCID 178506842, compound

Product 1

HCID 17917408HCID 17917408, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(3-(Methylphenylamino)-1H-indenyl)lithium (3.10 g, 13.64 mmol) was dissolved in 50 mL of THF and added dropwise to a solution of t-butylaminodimethylsilylchloride (2.17 g, 16.35 mmol) in 35 mL. of THF over a 30 minute period, with stirring continued for 25 hours. The solvent was evaporated and the resulting oil was subjected to vacuum for 4 hours. This oil was dissolved in 100 mL of hexane and filtered of from LiCl. Solvent removal in vacuo and overnight vacuum devolatilization provided the product (4.66g, 13.3 mmol) as a dark red oil in 98 percent yield.

Workup

  1. customThe solvent was evaporated
  2. waitthe resulting oil was subjected to vacuum for 4 hours
  3. dissolutionThis oil was dissolved in 100 mL of hexane
  4. filtrationfiltered of from LiCl
  5. customSolvent removal in vacuo and overnight vacuum devolatilization

Sources & evidence

ORD record
ord-0eefc89585c144438addc514aebe7314
Source dataset
uspto-grants-2001_07
Patent number
US06268444B1

Reaction notes

Loading…