Lithium hydroxide, monohydrate → 1-(4-Cyano-3-fluorobenzyl)-5-(hydroxymethyl)imidazole

HRID 379046Notes

Reaction equation

HRID 379046 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][C:5]=1[F:21])#[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][C:5]=1[F:21])#[N:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 18535996HCID 18535996, compound

Product 1

HCID 185360621-(4-Cyano-3-fluorobenzyl)-5-(hydroxymethyl)imidazole

Reagents, catalysts & solvents 1

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

Procedure

To a solution of 1-(4-cyano-3-fluorobenzyl)-5-(acetoxymethyl)imidazole hydrobromide (as described in Example 14, Step C) (31.87 g, 89.77 mmol) in 300 mL of 2:1 THF/water at 0° C. was added lithium hydroxide monohydrate (7.53 g, 179 mmol). After two hours, the reaction was concentrated in vacuo to a 100 mL volume, stored at 0° C. for 30 minutes, then filtered and washed with 700 mL of cold water to provide a brown solid. This material was dried in vacuo over P2O5 to provide the titled product as a pale brown powder which was sufficiently pure for use in the next step without further purification.

Workup

  1. concentrationthe reaction was concentrated in vacuo to a 100 mL volume
  2. waitstored at 0° C. for 30 minutes
  3. filtrationfiltered
  4. washwashed with 700 mL of cold water
  5. customto provide a brown solid
  6. dry with materialThis material was dried in vacuo over P2O5

Sources & evidence

ORD record
ord-e505ac673ba34873950ce566a65a0beb
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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