3-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)pyridine → HCID 178428961, compound

HRID 1757441Notes

Reaction equation

HRID 1757441 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:6][O:5][C:4]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:3]1.[C:14]1([Li])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[CH3:1][C:2]1([CH3:13])[CH2:6][O:5][C:4]([C:7]2[CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][NH:9][CH:8]=2)=[N:3]1

Participants

4

Reactant 2

HCID 27361293-(4,4-Dimethyl-4,5-dihydro-1,3-oxazol-2-yl)pyridineHCID 178506676HCID 178506676, compound

Product 1

HCID 178428961HCID 178428961, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (-78° C.) solution of 3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine [Hauck A. E., et al., J. Chem. Soc. Perkin I 1980:2070-2076] (140.0 g, 0.79 mol) in 500 mL dry tetrahydrofuran (THF), phenyllithium (1.42 mol, 1.8 eq) is added under a nitrogen atmosphere until gas chromatography (GC) analysis indicates no more starting material is present. The reaction mixture is stirred for 10 minutes and then quenched with 500 mL water at -78° C. After warming the reaction mixture to room temperature with a water bath, 700 mLof diethyl ether is added to the mixture. The resulting solid is filtered, rinsed once with chilled methanol, and then dried at 40° C. in a vacuum oven overnight to yield 166.6 g (0.65 mol) of 1,4-dihydro-3-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-4-phenylpyridine.

Workup

  1. additionis added under a nitrogen atmosphere until gas chromatography (GC) analysis
  2. customquenched with 500 mL water at -78° C
  3. addition700 mLof diethyl ether is added to the mixture
  4. filtrationThe resulting solid is filtered
  5. washrinsed once with chilled methanol
  6. customdried at 40° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-a71556cd8b6f4de894261217f9b40d62
Source dataset
uspto-grants-1995_08
Patent number
US05446057

Reaction notes

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