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

HRID 349963Notes

Reaction equation

HRID 349963 reaction equation
[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[O:9][C:10]([CH3:15])=[C:11]([CH2:13][OH:14])[N:12]=1.Cl[C:17]1[CH:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:20]=[CH:19][N:18]=1.O1CCC[CH2:28]1>O.CN(C)C=O>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[O:9][C:10]([CH3:15])=[C:11]([CH2:13][O:14][C:17]2[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:28])=[O:24])[CH:20]=[CH:19][N:18]=2)[N:12]=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

Sodium hydride (60%, oily, 2.88 g) was added to a mixture of 2-(2-furyl)-5-methyl-4-oxazolylmethanol (10.80 g), methyl 2-chloro-4-pyridinecarboxylate (10.30 g), tetrahydrofuran (100 ml) and N,N-dimethylformamide (100 ml) at 0° C., and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-4-pyridinecarboxylate (2.86 g, yield 15%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 80–81° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0e89e0d414a14951a27eb140600404db
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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