2-Ethoxycarbonyl-3-methylimidazo[5,1-b]thiazole → {3-Methylimidazo[4,3-b][1,3]thiazol-2-yl}methanol

HRID 1603439Notes

Reaction equation

HRID 1603439 reaction equation
B.[Na].C([O:5][C:6]([C:8]1[S:12][C:11]2=[CH:13][N:14]=[CH:15][N:10]2[C:9]=1[CH3:16])=O)C>C(O)C>[OH:5][CH2:6][C:8]1[S:12][C:11]2=[CH:13][N:14]=[CH:15][N:10]2[C:9]=1[CH3:16]

Participants

4

Reactant 2

HCID 196051332-Ethoxycarbonyl-3-methylimidazo[5,1-b]thiazoleHCID 178418435HCID 178418435, compound

Product 1

HCID 19605134{3-Methylimidazo[4,3-b][1,3]thiazol-2-yl}methanolYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1.56 g portion of sodium boron hydride was added to 60 ml of an ethanol solution containing 1.684 g of 2-ethoxycarbonyl-3-methylimidazo[5,1-b]thiazole, and the mixture was then stirred at room temperature for 4 days. The solvent was evaporated under reduced pressure, and water was then added thereto. The solution was extracted twice with dichloromethane, and the combined organic layer was dried over anhydrous magnesium sulfate and then filtered. Afterward, the solvent was evaporated under reduced pressure to obtain 1.33 g of the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water
  2. additionwas then added
  3. extractionThe solution was extracted twice with dichloromethane
  4. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customAfterward, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6282f628573d4a6e9f3f2186f4bb343a
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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