Borane → (Furo[3,2-c]pyridin-7-yl)methanol

HRID 910084Notes

Reaction equation

HRID 910084 reaction equation
B.[O:2]1[C:10]2[C:9]([C:11](O)=[O:12])=[CH:8][N:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1>O1CCCC1>[O:2]1[C:10]2[C:9]([CH2:11][OH:12])=[CH:8][N:7]=[CH:6][C:5]=2[CH:4]=[CH:3]1

Participants

4

Reactant 2

HCID 6331Borane3×HCID 17985520HCID 17985520, compound

Product 1

HCID 17985730(Furo[3,2-c]pyridin-7-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add Borane (1.0 M in tetrahydrofuran, 0.61 mL, 0.61 mmol) to a solution of furo[3,2-c]pyridine-7-carboxylic acid (0.100 g, 0.61 mmol) in tetrahydrofuran (2 mL) and stir for 1 hour. Add additional borane (0.61 mL) stir for 30 minutes, add additional borane (0.61 ml), quench with 1N HCl (10 mL) and stir for 15 minutes. Add aqueous ammonium hydroxide (28-30%, 3 mL), extract with diethyl ether, dry over magnesium sulfate, filter and concentrate to give the title compound as a white solid.

Workup

  1. stirringstir for 30 minutes
  2. customquench with 1N HCl (10 mL)
  3. stirringstir for 15 minutes
  4. extractionAdd aqueous ammonium hydroxide (28-30%, 3 mL), extract with diethyl ether
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-bd8ab2cfd9b04cbd8b52392f3140d6e6
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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