Water → 4-Hydroxyethyl-5-methyl-2-phenylimidazole

HRID 1760489Notes

Reaction equation

HRID 1760489 reaction equation
C([O:3][C:4]([CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:10][C:11]=1[CH3:12])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[OH:3][CH2:4][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:10][C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22597552Ethyl 5-methyl-2-phenylimidazole-4-acetate

Product 1

HCID 543635624-Hydroxyethyl-5-methyl-2-phenylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 4-ethoxycarbonylmethyl-5-methyl-2-phenylimidazole (19.7 g) in tetrahydrofuran (100 ml) was added dropwise (in 45 min) to lithium aluminium hydride (10 g) in tetrahydrofuran (150 ml). After 2 h refluxing the reaction mixture was allowed to stand overnight at r.t. It was cooled in an ice bath and water (40 ml) and tetrahydrofuran (50 ml) were added. The solids were filtered off and washed with diethylether.

Workup

  1. temperatureAfter 2 h refluxing the reaction mixture
  2. temperatureIt was cooled in an ice bath
  3. filtrationThe solids were filtered off
  4. washwashed with diethylether

Sources & evidence

ORD record
ord-8a360cf9f533446187ab97dca9eb016c
Source dataset
uspto-grants-2005_01
Patent number
US06841553B2

Reaction notes

Loading…