(2-Allyloxy-3-tert-butyl-5-methylphenyl)chlorodimethylsilane → (2-Dimethylamino-4,5-dimethylcyclopentadienyl)(2-allyloxy-3-tert-butyl-5-methylphenyl)dimethylsilane

HRID 724498Notes

Reaction equation

HRID 724498 reaction equation
[CH2:1]([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([CH3:15])=[CH:7][C:6]=1[Si:16]([CH3:19])([CH3:18])Cl)[CH:2]=[CH2:3].[CH3:20][N:21]([CH3:30])[C:22]1([Li])[CH:26]=[C:25]([CH3:27])[C:24]([CH3:28])=[CH:23]1>C1(C)C=CC=CC=1.O1CCCC1>[CH3:20][N:21]([CH3:30])[C:22]1[CH:26]([Si:16]([C:6]2[CH:7]=[C:8]([CH3:15])[CH:9]=[C:10]([C:11]([CH3:13])([CH3:14])[CH3:12])[C:5]=2[O:4][CH2:1][CH:2]=[CH2:3])([CH3:19])[CH3:18])[C:25]([CH3:27])=[C:24]([CH3:28])[CH:23]=1

Participants

5

Reactant 2

HCID 21880918(2-Allyloxy-3-tert-butyl-5-methylphenyl)chlorodimethylsilaneHCID 178506779HCID 178506779, compound

Product 1

HCID 58747148(2-Dimethylamino-4,5-dimethylcyclopentadienyl)(2-allyloxy-3-tert-butyl-5-methylphenyl)dimethylsilaneYield 102.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-allyloxy-3-tert-butyl-5-methylphenyl)dimethylchlorosilane (7.0 mmol) in toluene (12.1 mL) was added dropwise to a solution of 1-dimethylamino-3,4-dimethylcyclopentadienyllithium (7.0 mmol) in tetrahydrofuran (10.5 mL) and the mixture was stirred at room temperature for 6 hours. After the solvent was distilled off under reduced pressure, dehydrated pentane was added and a precipitated solid was filtered off. The filtrate was concentrated to obtain the title compound (2.86 g, 100%) as an oil.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. additionwas added
  3. filtrationa precipitated solid was filtered off
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-acdf963addc5423383edfa9cbf274e08
Source dataset
uspto-grants-2006_11
Patent number
US07141690B2

Reaction notes

Loading…