3-Pentanol → CP-316311

HRID 1637686Notes

Reaction equation

HRID 1637686 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.O1CCCC1>[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 120.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-pentanol (56 mL, 0.5205 mol) in dimethyl sulfoxide (DMSO, 760 mL) was added, portionwise, sodium hydride (60% oil dispersion, 7.64 g, 0.191 mol). After stirring at room temperature for thirty minutes, a solution of 4-chloro-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)-pyridine (prepared as described in Preparation D, 47.80 g, 0.1735 mol) in tetrahydrofuran (THF, 50 mL) was added and the resulting mixture was heated at 130° C. for three hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give 68.21 g of a yellow solid. The solid was purified through silica gel column chromatography using 10% chloroform in hexane to chloroform as eluent to give 52.2064 g (92%) of the title compound of Example 2 as white crystals. mp 72.5° C. to 74° C. 1HNMR (CDCl3) δ 6.84 (s, 2H), 6.26 (s,1 H), 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 three hours
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2fd2b53f51f44a0d86e70c05278882bb
Source dataset
uspto-grants-2000_03
Patent number
US06043260

Reaction notes

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