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

HRID 399136Notes

Reaction equation

HRID 399136 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-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-6129e6f08f1f42c0993050cda4f3a2b3
Source dataset
uspto-grants-1998_10
Patent number
US05817678

Reaction notes

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