Lithium hydroxide, monohydrate → HCID 19072504, compound

HRID 1955730Notes

Reaction equation

HRID 1955730 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]C)=[O:22])=[CH:16][CH:15]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].O.[OH-].[Li+]>O1CCOCC1.O.O>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:18][CH:19]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 19072540HCID 19072540, compound

Product 1

HCID 19072504HCID 19072504, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

3.3 g (9.5 mmol) of methyl 2-[4-(2-butyl-4-chloro-5-formyl-imidazol-1-yl-methyl)-phenyl]-acetate are dissolved in 100 ml of dioxane/water (1:1) at 0° C. and a solution of 0.44 g (10.4 mmol) of lithium hydroxide monohydrate in 5 ml of water is added dropwise with stirring. After stirring at room temperature for 3 h, the mixture is concentrated to a half, diluted with water, washed with diethyl ether, and the aqueous phase is acidified with 1N hydrochloric acid and extracted three times with ethyl acetate. The combined ethyl acetate phases are dried over sodium sulphate and concentrated.

Workup

  1. stirringAfter stirring at room temperature for 3 h
  2. concentrationthe mixture is concentrated to a half
  3. additiondiluted with water
  4. washwashed with diethyl ether
  5. extractionextracted three times with ethyl acetate
  6. dry with materialThe combined ethyl acetate phases are dried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a534940944104350a157a2cc5e8b77cf
Source dataset
uspto-grants-1998_07
Patent number
US05776964

Reaction notes

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