Diisobutylaluminum hydride → HCID 22257665, compound

HRID 1250534Notes

Reaction equation

HRID 1250534 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-64354aa67f7640429510ea21020a0916
Source dataset
uspto-grants-2002_01
Patent number
US06339087B1

Reaction notes

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