Water → 8-(2-Ethyl-6-methylbenzyloxy)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine

HRID 1386079Notes

Reaction equation

HRID 1386079 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:12]1[N:16]2[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:22][C:23]3[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=3[CH2:30][CH3:31])[C:15]2=[N:14][C:13]=1[CH3:32])(OCC)=[O:8].O.[OH-].[Na+]>O1CCCC1>[CH2:30]([C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:23]=1[CH2:22][O:21][C:20]1[C:15]2[N:16]([C:12]([CH2:7][OH:8])=[C:13]([CH3:32])[N:14]=2)[CH:17]=[CH:18][CH:19]=1)[CH3:31]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 217173563-Carboethoxy-8-(2-ethyl-6-methylbenzyloxy)-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 217173318-(2-Ethyl-6-methylbenzyloxy)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of LiAlH4 (0.08 g, 2.1 mmol) in tetrahydrofuran (25 ml) was added 3-carboethoxy-8-(2-ethyl-6-methylbenzyloxy)-2-methylimidazo[1,2-a]pyridine (1.0 g, 2.8 mmol) in tetrahydrofuran (25 ml). After stirring the mixture at room temperature for 2 h., 0.2 ml of water was added dropwise, followed by 0.2 ml of 15% sodium hydroxide and then 0.6 ml of water. The solids were removed by filtration and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel using methylene chloride:methanol (9:1) as eluent. Crystallization from diethyl ether gave 0.52 g (60%) of the title compound.

Workup

  1. customThe solids were removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel
  4. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-58fd5db54c6d4484986cbad8df23fc98
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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