Lithium hydroxide, monohydrate → 1-(4-Cyanobenzyl)-5-hydroxymethyl-1H-imidazole

HRID 365462Notes

Reaction equation

HRID 365462 reaction equation
Br.[C:2]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][N:9]2[C:13]([CH2:14][O:15]C(=O)C)=[CH:12][N:11]=[CH:10]2)=[CH:6][CH:5]=1)#[N:3].O.[OH-].[Li+]>C1COCC1.O>[C:2]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][N:9]2[C:13]([CH2:14][OH:15])=[CH:12][N:11]=[CH:10]2)=[CH:6][CH:5]=1)#[N:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57427559HCID 57427559, compound

Product 1

HCID 101982471-(4-Cyanobenzyl)-5-hydroxymethyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

1-(4-Cyanobenzyl)-5-(acetoxymethyl)-imidazole hydrobromide (50.4 g, 150 mmol) in 3:1 THF/water (1.5 L) at 0° C. was added lithium hydroxide monohydrate (18.9 g, 450 mmol). After 1 hr, the reaction was concentrated in vacuo, diluted with EtOAc (3 L), and washed with water, sat. aq. NaHCO3 and brine. The solution was then dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product as a pale yellow fluffy solid which was sufficiently pure for use in the next step without further purification.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. additiondiluted with EtOAc (3 L)
  3. washwashed with water, sat. aq. NaHCO3 and brine
  4. dry with materialThe solution was then dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7eba954fb1ac444790f9700f3ad522b5
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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