3-(2-(Tetrahydropyran-2-yloxy)ethoxy)pyridine → 2-(Pyridin-3-yloxy)ethan-1-ol

HRID 1384644Notes

Reaction equation

HRID 1384644 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1>C(O)(=O)C.C1COCC1.O>[OH:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 1

HCID 226248913-(2-(Tetrahydropyran-2-yloxy)ethoxy)pyridine

Product 1

HCID 219089972-(Pyridin-3-yloxy)ethan-1-olYield 86%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(2-(tetrahydropyran-2-yloxy)ethoxy)pyridine (1.54 g, 7 mmol) in acetic acid (8 ml), THF (4 ml) and water (2 ml) was heated at 50° C. for 4 hours. The volatiles were removed by evaporation and the residue azeotroped with toluene to give 3-(2-hydroxyethoxy)pyridine (820 mg, 86%) as an off-white solid. 1H NMR Spectrum: (DMSOd6) 3.70(t, 2H); 4.05(t, 2H); 4.85(s, 1H); 7.25(dd, 1H); 7.37(dd, 1H); 8.10(d, 1H); 8.24(d, 1H) MS-ESI: 140 [MH]+

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue azeotroped with toluene

Sources & evidence

ORD record
ord-d991e0b233114f8486ed684d3f2a8f84
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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