Water → HCID 131727126, compound

HRID 15712Notes

Reaction equation

HRID 15712 reaction equation
[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH3:26])[C:20]=1[Li].C1(C)C=CC=CC=1.O>O1CCCC1>[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]([C:20]2[C:21]([CH3:26])=[CH:22][C:23]([CH3:25])=[CH:24][C:19]=2[CH3:18])=[NH:13])[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 131727127HCID 131727127, compoundHCID 178506704HCID 178506704, compound

Product 1

HCID 131727126HCID 131727126, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzonitrile (6.3 mmol) in tetrahydrofuran (25.5 mL) was added dropwise a solution of 2,4,6-trimethylphenyllithium (12.5 mmol) in tetrahydrofuran (55.6 mL) at −78° C. under a nitrogen atmosphere. The temperature of the mixture was raised to room temperature and the mixture was stirred for 5 hrs. To the reaction mixture solution were added toluene and water to separate an organic layer and an aqueous layer. The organic layer was dried and the solvent was distilled off to give 2-(2,3,4,5-tetramethylcyclopentadienyl)-α-(2,4,6-trimethylphenyl)-benzenemethanimine (2.34 g) as a brown oily substance.

Workup

  1. customto separate an organic layer
  2. customThe organic layer was dried
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-29feb4137b0441c781c0527555c2770c
Source dataset
uspto-grants-2010_06
Patent number
US07732643B2

Reaction notes

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