Tetrahydrofuran → Ethyl 2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-4-pyridinecarboxylate

HRID 1294166Notes

Reaction equation

HRID 1294166 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:13])=[C:9]([CH2:11][OH:12])[N:10]=1.Cl[C:15]1[CH:20]=[C:19]([C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:17][N:16]=1.O1CCC[CH2:26]1.[H-].[Na+]>O.CN(C)C=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:13])=[C:9]([CH2:11][O:12][C:15]2[CH:20]=[C:19]([C:21]([O:23][CH2:24][CH3:26])=[O:22])[CH:18]=[CH:17][N:16]=2)[N:10]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 178612042-(2-Furyl)-5-methyl-4-oxazolylmethanol

Product 1

HCID 68883945Ethyl 2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-4-pyridinecarboxylateYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(2-furyl)-5-methyl-4-oxazolylmethanol (10.8 g), methyl 2-chloro-4-pyridinecarboxylate (10.3 g) and a solution of tetrahydrofuran (100 mL) and N,N-dimethylformamide (100 mL) was added sodium hydride (60%, oil, 2.88 g) at 0° C. and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give ethyl 2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-4-pyridinecarboxylate (2.86 g, yield 15%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, v/v). The crystals were recrystallized from ethyl acetate-hexane. melting point: 80-81.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c166ebfb3bf149a1803f81e46a361137
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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