Sodium hydride → Methyl 6-(5-methyl-2-phenyl-4-oxazolyl)methoxy-2-pyridinecarboxylate

HRID 1294141Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][OH:14].[H-].[Na+].[H][H].Cl[C:20]1[N:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=1>O1CCCC1.O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:20]1[N:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of (5-methyl-2-phenyl-4-oxazolyl)methanol (8.51 g) and tetrahydrofuran (100 mL) was added sodium hydride (60%, oil, 1.80 g) at room temperature and the reaction mixture was stirred at room temperature until generation of hydrogen ended. The mixture was added to a solution of methyl 6-chloropyridine-2-carboxylate (7.72 g) in tetrahydrofuran (75 ml) at room temperature and the obtained mixture was further stirred at 40° C. for 5 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals of methyl 6-(5-methyl-2-phenyl-4-oxazolyl)methoxy-2-pyridinecarboxylate from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave pale-yellow plate crystals (7.41 g, 51%). melting point: 97-98° C.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed successively with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-6454366ac18949dca5886c1874e273b0
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238716B2

Reaction notes

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