Water → ethyl 3-ethoxy-1-[6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethyl]-1H-pyrazol-4-ylacetate

HRID 350259Notes

Reaction equation

HRID 350259 reaction equation
[H-].[Na+].Cl[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[O:20][CH:21]=[CH:22][CH:23]=3)[O:16][C:17]=2[CH3:18])=[N:9][CH:10]=1.[CH2:24]([O:26][C:27]1[C:31]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:30][NH:29][N:28]=1)[CH3:25].O>CN(C)C=O>[CH2:24]([O:26][C:27]1[C:31]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:30][N:29]([CH2:4][C:5]2[CH:10]=[N:9][C:8]([O:11][CH2:12][C:13]3[N:14]=[C:15]([C:19]4[O:20][CH:21]=[CH:22][CH:23]=4)[O:16][C:17]=3[CH3:18])=[CH:7][CH:6]=2)[N:28]=1)[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 230763795-Chloromethyl-2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]pyridineHCID 178470746HCID 178470746, compound

Product 1

HCID 69426925ethyl 3-ethoxy-1-[6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethyl]-1H-pyrazol-4-ylacetateYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 39.4 mg) was added to a solution of 5-chloromethyl-2-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]pyridine (300 mg), ethyl 3-ethoxy-1H-pyrazol-4-ylacetate (195 mg) in N,N-dimethylformamide (10 ml) at 0° C., and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and 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 3-ethoxy-1-[6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethyl]-1H-pyrazol-4-ylacetate (364 mg, yield 79%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. extractionextracted 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-984ee5736c0b42df9714c30c89cc408f
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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