Furo[3,2-c]pyridine-2-carbaldehyde → Furo[3,2-c]pyridin-2-ylmethanol

HRID 217162Notes

Reaction equation

HRID 217162 reaction equation
[BH4-].[Na+].[O:3]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[CH:5]=[C:4]1[CH:12]=[O:13]>CO>[O:3]1[C:11]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[CH:5]=[C:4]1[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 642131Furo[3,2-c]pyridine-2-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 57659570Furo[3,2-c]pyridin-2-ylmethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (0.26 g, 6.8 mmol) was added to a stirred solution of furo[3,2-c]pyridine-2-carbaldehyde (2.00 g, 13.6 mmol) in anhydrous MeOH (25 mL) at 0° C. After 1.5 h, the reaction was quenched with H2O (20 mL), before being extracted with CH2Cl2 (3×30 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated to provide the title compound: m/z (ES+)=150.0 [M+H]+.

Workup

  1. customthe reaction was quenched with H2O (20 mL)
  2. extractionbefore being extracted with CH2Cl2 (3×30 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a36426abc189488083503a47c27ba46f
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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