Sodium hydride → HCID 66718199, compound

HRID 1514670Notes

Reaction equation

HRID 1514670 reaction equation
[C:1]1([C:7]2[C:11]([CH2:12][OH:13])=[C:10](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:25]1[N:30]=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=1>C1COCC1>[CH3:34][O:33][C:31](=[O:32])[C:28]1[CH:27]=[CH:26][C:25]([O:13][CH2:12][C:11]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:8][O:9][C:10]=2/[CH:14]=[CH:15]/[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[N:30][CH:29]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 66718159HCID 66718159, compound

Product 1

HCID 66718199HCID 66718199, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of [3-phenyl-5-((E)-styryl)-isoxazol-4-yl]-methanol (1.50 g, 5.4 mmol) in THF (50 mL) was cooled in an ice bath. Sodium hydride (0.28 g of a 55% dispersion in mineral oil, 6.4 mmol) was added and the mixture was stirred for 30 min whilst allowing to warm to room temperature. To the resulting suspension was added methyl 6-chloropyridine-3-carboxylate (0.93 g, 5.4 mmol). After stirring for 2 h the reaction mixture was quenched with aqueous saturated sodium bicarbonate solution (20 mL). Evaporation of the organic solvent was followed by extraction with ethyl acetate. The organic phase was dried over sodium sulfate, filtered, concentrated and purified by chromatography (silica, heptane:ethyl acetate=90:10 to 60:40) to afford the title compound as an off-white solid (0.78 g, 35%). MS: m/e=413.5 [M+H]+.

Workup

  1. stirringAfter stirring for 2 h the reaction mixture
  2. customwas quenched with aqueous saturated sodium bicarbonate solution (20 mL)
  3. customEvaporation of the organic solvent
  4. extractionwas followed by extraction with ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by chromatography (silica, heptane:ethyl acetate=90:10 to 60:40)

Sources & evidence

ORD record
ord-0c95345c6c8a4b16920881295f5534ab
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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