Sodium hydride → HCID 22625095, compound

HRID 1384548Notes

Reaction equation

HRID 1384548 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.Br[CH2:11][CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1>CN(C=O)C.O>[O:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH:14]1[O:13][CH2:12][CH2:11][N:7]1[CH:8]=[CH:9][C:4](=[O:3])[CH:5]=[CH:6]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 178418642HCID 178418642, compound

Product 1

HCID 22625095HCID 22625095, compoundYield 28.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Sodium hydride (1.27 g of a 50% suspension in mineral oil, 26.4 mmol) was added to a solution of 4-hydroxypyridine (2.5 g, 26 mmol) in DMF (50 ml) and the mixture stirred for 30 minutes. 2-(2-Bromoethoxy)tetrahydropyran (5.0 g, 23.9 mmol), (J. Am. Chem. Soc. 1948, 70, 4187), in DMF (5 ml) was added and the mixture heated at 80° C. for 3 hours. The reaction mixture was allowed to cool, diluted with water and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3) to give 1-[2-(tetrahydropyran-2-yloxy)ethyl]-1,4-dihydro-4-pyridone (1.5 g, 28%). 1H NMR Spectrum: (DMSOd6) 1.39-1.68(m, 6H); 3.39-3.44(m, 1H); 3.64-3.78(m, 2H); 3.86-3.92(m, 1H); 4.20(t, 2H); 4.64(s, 1H); 6.95(d, 2H); 8.36(d, 2H) MS-ESI: 224 [MH]+

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3)

Sources & evidence

ORD record
ord-a75e37f530e642cead0e6faf332b7b29
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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