Ammonium Chloride → (2H-[1,3]Dioxolo[4,5-b]pyridin-2-yl)methanol

HRID 1793306Notes

Reaction equation

HRID 1793306 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[O:3][CH:2]1[C:10](OC)=[O:11].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1.O.C(OCC)(=O)C>[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[O:3][CH:2]1[CH2:10][OH:11]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 22020963HCID 22020963, compound

Product 1

HCID 22020937(2H-[1,3]Dioxolo[4,5-b]pyridin-2-yl)methanolYield 43.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Reaction under a nitrogen atmosphere. A solution of intermediate (4) (0.042 mol) in THF (48 ml) was added dropwise to LiAlH4 (1 Min THF) (0.0466 mol) and cooled with an ice-water bath. The resulting reaction mixture was stirred for one hour at room temperature. The reaction mixture was treated carefully with a 10% NH4Cl solution and it was diluted with water and ethyl acetate. The reaction mixture was filtered over Celite and the filtrate was extracted. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was washed with DCM, filtered off and dried, yielding 2.78 g of (±)-1,3-dioxolo[4,5-b]pyridine-2-methanol (intermediate 5).

Workup

  1. customReaction under a nitrogen atmosphere
  2. temperaturecooled with an ice-water bath
  3. customThe resulting reaction mixture
  4. filtrationThe reaction mixture was filtered over Celite
  5. extractionthe filtrate was extracted
  6. customThe separated organic layer was dried
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. washThe residue was washed with DCM
  10. filtrationfiltered off
  11. customdried

Sources & evidence

ORD record
ord-52bd9af9abde4dd88619b3dcdc6bb275
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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