Ethanol → 3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethanol

HRID 965851Notes

Reaction equation

HRID 965851 reaction equation
Cl[C:2]1[N:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]2[CH:11]=[CH:10][CH2:9][O:8][C:7]=12.CCO.[OH-].[Na+]>[Pd]>[O:8]1[C:7]2=[CH:2][N:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]2[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 22313337HCID 22313337, compound

Product 1

HCID 223133613,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethanolYield 89%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(8-Chloro-2H-pyrano[2,3-c]pyridin-6-yl)methanol (988 mg, 5.0 mmol) is combined with 100 mg 10% Pd/C in 25 ml EtOH containing 3 ml (6 mmol) of 2N aqueous NaOH in a 250 ml PARR shaker bottle. The reaction is hydrogenated at 50 PSI for 48 h, the catalyst is removed by filtration, and the filtrate is concentrated to dryness. The mixture is partitioned between 1×10 ml 1:1 saturated NaCl/conc. NH4OH and 4×10 ml CH2Cl2 and the combined organic layer is dried (K2CO3). The mixture is concentrated in vacuo to give 730 mg (89%) of 3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethanol as an off-white solid. HRMS (FAB) calcd for C9H11NO2+H: 166.0868, found 166.0868 (M+H)+.

Workup

  1. customthe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated to dryness
  3. customThe mixture is partitioned between 1×10 ml 1:1 saturated NaCl/conc
  4. dry with materialNH4OH and 4×10 ml CH2Cl2 and the combined organic layer is dried (K2CO3)
  5. concentrationThe mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-cf223513a5b4418a99cbe25044245371
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

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