Red-Al → 2,6-Dimethyl-8-(2,6-dimethylbenzyloxy)-3-hydroxymethylimidazo[1,2-a]pyridine

HRID 1386073Notes

Reaction equation

HRID 1386073 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[C:13]([C:18]1[N:22]2[CH:23]=[C:24]([CH3:37])[CH:25]=[C:26]([O:27][CH2:28][C:29]3[C:34]([CH3:35])=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:36])[C:21]2=[N:20][C:19]=1[CH3:38])(OCC)=[O:14]>C1(C)C=CC=CC=1>[CH3:38][C:19]1[N:20]=[C:21]2[C:26]([O:27][CH2:28][C:29]3[C:34]([CH3:35])=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:36])=[CH:25][C:24]([CH3:37])=[CH:23][N:22]2[C:18]=1[CH2:13][OH:14]

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 217173413-Carboethoxy-2,6-dimethyl-8-(2,6-dimethylbenzyloxy)imidazo[1,2-a]pyridine

Product 1

HCID 217173452,6-Dimethyl-8-(2,6-dimethylbenzyloxy)-3-hydroxymethylimidazo[1,2-a]pyridineYield 58.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of vitride (3 ml, 10.2 mmol) in toluene (3 ml) was added dropwise to nitrogene-purged solution of 3-carboethoxy-2,6-dimethyl-8-(2,6-dimethylbenzyloxy)imidazo[1,2-a]pyridine (0.68 g, 1.93 mmol) in toluene (15 ml). The ice-bath was removed and the reaction mixture was stirred at room temp. For 2 h and 15 min. The reaction mixture was cooled to 0° C. and quenched by addition of water (6 ml). Methylene chloride/methanol was added and the reaction mixture was filtered. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel, using methylene chloride:methanol (100:5) as eluent to give 0.35 g (58%) of the title compound.

Workup

  1. additionwas added dropwise
  2. customThe ice-bath was removed
  3. custom15 min
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. customquenched by addition of water (6 ml)
  6. additionMethylene chloride/methanol was added
  7. filtrationthe reaction mixture was filtered
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7f67038ff6704e92bd54f87b0ab7adf3
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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