Tetrahydrofuran → HCID 18548931, compound

HRID 1266269Notes

Reaction equation

HRID 1266269 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH:4]1CCCO.Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1.[O:23]1C[CH2:26][CH2:25][CH2:24]1>>[N:3]1([CH2:26][CH2:25][CH2:24][O:23][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=2)[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 18548932HCID 18548932, compound

Product 1

HCID 18548931HCID 18548931, compound

Procedure

To a cooled (0° C., ice bath) suspension of NaH (0.96 g, 20 mmol) in anhydrous tetrahydrofuran (100 ml) was added 3-morpholin-propanol (2.9 g, 20 mmol) under argon. This solution was stirred for an additional 1 hr. A solution of 2-chloro-5-nitropyridine (3.2 g, 20 mmol) in tetrahydrofuran (20 ml) was added all at once, and the resulting mixture was heated at reflux for 5 hrs under argon. After cooling, the solvent was removed by rotary evaporation, and the residue was dissolved in ethyl acetate. The ethyl acetate layer was washed (brine), dried (Na2SO4) and concentrated to dryness. The residue was chromatographed (flash column, silica gel, 10% ether in CH2Cl2) to give the title compound. mass spectrum (electrospray, m/e): 267.9 (M+H); IR cm-1: 2955, 1603, 1579, 1515; H-NMR δ (CDCl3): 1.95-2.05 (2H, m), 2.46-2.54 (6H, m), 3.71-3.74 (4H, m), 4.489 (2H, t), 6.812 (1H, d, C3-H), 8.49 (1H, dd, C4-H), 9.065 (1H, d, C5-H).

Workup

  1. temperatureTo a cooled
  2. temperaturewas heated
  3. temperatureat reflux for 5 hrs under argon
  4. temperatureAfter cooling
  5. customthe solvent was removed by rotary evaporation
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washThe ethyl acetate layer was washed (brine)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to dryness
  10. customThe residue was chromatographed (flash column, silica gel, 10% ether in CH2Cl2)

Sources & evidence

ORD record
ord-79a677abec474d57bc2cadf153a338e3
Source dataset
uspto-grants-2003_04
Patent number
US06548496B2

Reaction notes

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