Diisobutyl aluminium chloride → [8-(Dimethylamino)naphth-1-yl]diisobutylaluminium

HRID 898105

Reaction equation

HRID 898105 reaction equation
[Cl-].[CH2:2]([Al+:6][CH2:7][CH:8]([CH3:10])[CH3:9])[CH:3]([CH3:5])[CH3:4].[CH3:11][N:12]([CH3:24])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[C:21]([Li])=[CH:20][CH:19]=[CH:18]2>C(OCC)C>[CH3:11][N:12]([CH3:24])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[C:21]([Al:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:2][CH:3]([CH3:5])[CH3:4])=[CH:20][CH:19]=[CH:18]2

Participants

4

Reactant 2

HCID 16686353Diisobutyl aluminium chlorideHCID 178506672HCID 178506672, compound

Product 1

HCID 72359367[8-(Dimethylamino)naphth-1-yl]diisobutylaluminiumYield 70,907.102%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

9.5 g (0.048 mmol) of diisobutylaluminium chloride were added dropwise to a suspension, cooled to −40° C., of 12.1 g (0.048 mmol) of [8-(dimethylamino)naphth-1-yl]lithium etherate and 100 ml of diethyl ether in an inert nitrogen atmosphere. After slow warming to room temperature, the mixture was stirred for a further 24 hours in order to complete the reaction. Filtration through a D4 frit and removal of the solvent by distillation gave 10.6 g of [8-(dimethylamino)naphth-1-yl]diisobutylaluminium (71%) as a colourless, oily liquid by fractional distillation from the residue.

Workup

  1. customthe reaction
  2. filtrationFiltration
  3. customthrough a D4 frit and removal of the solvent
  4. distillationby distillation

Sources & evidence

ORD record
ord-57bb6f8ddb4c451aaa3533668a37e62f
Source dataset
uspto-grants-2008_04
Patent number
US07351678B2

Linked notes

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