Diisobutylaluminum hydride → HCID 22257665, compound

HRID 1610904Notes

Reaction equation

HRID 1610904 reaction equation
CC(C[AlH]CC(C)C)C.[Cl:10][C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:14][N:15]1[CH2:25][CH2:24][CH:18]([C:19](OCC)=[O:20])[CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH2:14][N:15]1[CH:16]=[CH:17][C:18]([CH:19]=[O:20])=[CH:24][CH2:25]1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 516892Sodium BicarbonateHCID 754129HCID 754129, compound

Product 1

HCID 22257665HCID 22257665, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 1.5 M solution of DIBAL-H™ in toluene (1.27 ml, 1.90 mmol) was added dropwise over 10 min. to a solution of ethyl 1-(3,4-dichlorobenzyl)isonipecotate (500 mg, 1.58 mmol) in toluene solution (5 ml) at −78° C. After 40 min., aqueous sodium bicarbonate solution was added and the reaction mixture was warmed to room temperature. The product was extracted into diethyl ether. The organic layer was dried over magnesium sulfate, filtered and concentrated to provide 1-(3,4-dichlorobenzyl)-4-formylpyridine (430 mg) as an oil.

Workup

  1. extractionThe product was extracted into diethyl ether
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ff1afeec716a4a958076c70ec18d3b64
Source dataset
uspto-grants-2006_01
Patent number
US06984637B2

Reaction notes

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