Ammonium Chloride → 2H-Pyrano[3,2-b]pyridine-3-methanol

HRID 1793320Notes

Reaction equation

HRID 1793320 reaction equation
[O:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11](OCC)=[O:12])[CH2:2]1.[BH4-].[Na+].[NH4+].[Cl-]>CO.C1COCC1>[O:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][OH:12])[CH2:2]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 858001942H-Pyrano[3,2-b]pyridine-3-carboxylic acid, ethyl ester

Product 1

HCID 220209432H-Pyrano[3,2-b]pyridine-3-methanolYield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of intermediate (24) (0.0032 mol) in methanol (dry) (2 ml) and THF (dry) (16 ml) was stirred at 0° C. NaBH4 (0.0128 mol) was added portionwise at 0° C. The reaction mixture was stirred for 5 hours at room temperature. A 10% NH4Cl solution was added and this mixture was extracted with DCM. The separated organic layer was dried, filtered and the solvent evaporated, yielding 0.45 g of 2H-pyrano[3,2-b]pyridine-3-methanol (intermediate 25).

Workup

  1. extractionthis mixture was extracted with DCM
  2. customThe separated organic layer was dried
  3. filtrationfiltered
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-495ba84ac0e447cda9911ec26109657e
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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