Tetrahydrofuran → (5-Phenylpyridin-2-yl)methanol

HRID 349998Notes

Reaction equation

HRID 349998 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][N:7]=1)(=O)C.[OH-].[Na+].O1CCCC1>CO>[C:12]1([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][OH:4])=[N:7][CH:8]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 230250605-Phenyl-2-pyridylmethyl acetate

Product 1

HCID 54044516(5-Phenylpyridin-2-yl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-phenyl-2-pyridylmethyl acetate (3.68 g), a 1N aqueous sodium hydroxide solution (30 ml), tetrahydrofuran (30 ml) and methanol (300 ml) was stirred at room temperature for 3 hours, which was concentrated. The residue was dissolved in ethyl acetate, and then the solution was washed with water, then with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residual colorless crystals were collected by filtration to obtain 5-phenyl-2-pyridylmethanol (2.84 g, yield 95%). This was recrystallized from ethyl acetate-hexane. Melting point: 86–87° C.

Workup

  1. concentrationwhich was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed with water
  4. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  5. concentrationconcentrated
  6. filtrationThe residual colorless crystals were collected by filtration

Sources & evidence

ORD record
ord-77546c6d00d646a6a1a9a794377f37e5
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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