Tetrahydrofuran → (6-Methylpyridin-3-yl)methanol

HRID 392467Notes

Reaction equation

HRID 392467 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[C:8]1[C:13]([C:14]([O:16]C)=O)=[CH:12][N:11]=[CH:10][CH:9]=1.O1CCC[CH2:19]1>O.[OH-].[Na+]>[CH3:19][C:10]1[N:11]=[CH:12][C:13]([CH2:14][OH:16])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 10877301methyl 4-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a slurry of lithium aluminum hydride (500 mg, 13.2 mmol) in anhydrous tetrahydrofuran (45 mL) at 0° C. under nitrogen was added dropwise a solution of methyl 4-methylnicotinate (15, 1.0 g, 6.6 mmol) in anhydrous tetrahydrofuran (5 mL). After 1.5 h the suspension was diluted with water (1 mL) and 6 N NaOH solution (5 mL). The precipitate was removed by vacuum filtration and the filtrate was dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to provide the title compound as a light yellow oil: 1H NMR (300 MHz) 8.34 (s, 1H), 7.60 (d, J=7.9 Hz, 1H), 7.12 (d, J=7.9 Hz, 1H), 4.65 (s, 2H), 4.18-4.10 (bs, 1H), 2.51 (s, 3H) ppm.

Workup

  1. customThe precipitate was removed by vacuum filtration
  2. dry with materialthe filtrate was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-87ccb7c706924bf981a55c4ce907bef4
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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