Sodium Hydroxide → 8-Benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine

HRID 4304Notes

Reaction equation

HRID 4304 reaction equation
Cl.[CH2:2]([O:9][C:10]1[C:11]2[N:12]([C:16]([CH2:20][O:21][CH2:22][C:23]#[CH:24])=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>O>[CH2:2]([O:9][C:10]1[C:11]2[N:12]([C:16]([CH2:20][O:21][CH2:22][C:23]#[CH:24])=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 201523238-Benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine hydrochloride

Product 1

HCID 138259158-Benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridineYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8-benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine hydrochloride (35.5 g) in hot water (700 ml) was neutralized with aqueous sodium hydroxide solution and extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate, treated with activated charcoal, and evaporated in vacuo. The residual solid was recrystallized from a mixture of methylene chloride and n-hexane to give 8-benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (26.03 g).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. additiontreated with activated charcoal
  5. customevaporated in vacuo
  6. customThe residual solid was recrystallized from a mixture of methylene chloride and n-hexane

Sources & evidence

ORD record
ord-0b010a06534749b3b7cbeed2aa29438d
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Reaction notes

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