3-Pentanol → CP-316311

HRID 1831630Notes

Reaction equation

HRID 1831630 reaction equation
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[C:15]([CH3:16])=[C:14]([O:17][C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[N:13]=[C:12]([CH3:27])[CH:11]=1>CS(C)=O.C1COCC1>[CH2:2]([CH:3]([O:6][C:10]1[CH:11]=[C:12]([CH3:27])[N:13]=[C:14]([O:17][C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[C:15]=1[CH3:16])[CH2:4][CH3:5])[CH3:1]

Participants

6

Reactant 3

HCID 114283-PentanolHCID 24758Sodium hydrideHCID 99036754-Chloro-2,5-dimethyl-6-(2,4,6-trimethyl-phenoxy)pyridine

Product 1

HCID 9818802CP-316311Yield 6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-pentanol (0.2 ml, 0.5205 mol) in DMSO (1 ml) was added 60% sodium hydride in oil (30 mg) in a portionwise. After stirring at room temperature for 5 min, a solution of 4-chloro-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)-pyridine (98 mg) in 0.5 ml of dry THF was added and the resulting mixture was heated at 130° C. for 5 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give a yellow solid. The solid was purified through silica gel column chromatography using 20% chloroform in hexane to chloroform as eluent to give 7 mg of the title compound as white crystals, mp 72.5–74° C. 1H NMR (CDCl3) δ 6.84 (s, 2H), 6.26 (s, 1H), 4.16 (m, 1H), 2.27 (s, 3H), 2.17 (s, 6H), 2.04 (s, 6H), 1.69 (m, 4H), 0.95 (t, 6H) ppm.

Workup

  1. temperaturethe resulting mixture was heated at 130° C. for 5 hours
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. customto give a yellow solid
  8. customThe solid was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-7338d66fcf0442588ec31e49b870b3f6
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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