Tetrahydrofuran → HCID 178519339, compound

HRID 1854664Notes

Reaction equation

HRID 1854664 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=O)=[CH:9][C:4]=2[N:3]=N1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S([O-])(=O)=O.[Na+].[Na+].O1CCC[CH2:27]1>>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][OH:12])=[CH:9][C:4]=2[N:3]=[CH:27]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24436Sodium Sulfate2×HCID 21226445Aluminium lithium hydrideHCID 178524184HCID 178524184, compound

Product 1

HCID 178519339HCID 178519339, compoundYield 16%

Conditions

Temperature
70 °C

Procedure

To a solution of 1H-benzotriazole-5-carboxylic acid (1.00 g, 6.13 mmol) in 30 mL of dry tetrahydrofuran was added lithium aluminum hydride (0.47 g, 12 mmol) under nitrogen at 0° C. After the reaction mixture was stirred at 70° C. for 90 h, saturated Na2SO4 aqueous solution was added carefully at 0° C. After the solution was stirred at room temperature for 30 min, a sufficient amount of Na2SO4 was added with additional stirring for drying. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (chloroform/methanol=97/3 to 80/20) to obtain (1H-benzoimidazol-5-yl)methanol as a pale yellow solid (143 mg, 16%).

Workup

  1. stirringAfter the solution was stirred at room temperature for 30 min
  2. stirringwith additional stirring
  3. customfor drying
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel column chromatography (chloroform/methanol=97/3 to 80/20)

Sources & evidence

ORD record
ord-a11eadda0774448db5872e8ae0dd36ed
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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