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

HRID 1416532Notes

Reaction equation

HRID 1416532 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 574275591-(4-Cyanobenzyl)-5-(acetoxymethyl)imidazole hydrobromide

Product 1

HCID 101982471-(4-Cyanobenzyl)-5-hydroxymethyl-1H-imidazoleYield 82%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of the acetate 4 (50.4 g) in 1.5 L of 3:1 THF/water at 0° C. was added lithium hydroxide monohydrate (18.9 g). After one hour, 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 (26.2 g) 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-1500500f2f1c4e72b080d98b962371a1
Source dataset
uspto-grants-1999_06
Patent number
US05914341

Reaction notes

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