Water → HCID 57736353, compound

HRID 2261358Notes

Reaction equation

HRID 2261358 reaction equation
[OH:1][C:2]([C:5]1[O:9][N:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=1)([CH3:4])[CH3:3].[H-].[Na+].Br[CH2:18][C:19]#[CH:20].O>O1CCCC1>[CH3:3][C:2]([C:5]1[O:9][N:8]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=1)([O:1][CH2:20][C:19]#[CH:18])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 16764416HCID 16764416, compound

Product 1

HCID 57736353HCID 57736353, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.00 g of ethyl 5-(1-hydroxy-1-methylethyl)isoxazole-3-carboxylate was dissolved in 20 ml of tetrahydrofuran, and 0.44 g of sodium hydride and 1.32 g of 3-bromo-1-propyne were then added under ice-cooling. The mixture was stirred at room temperature for 5 hours. After water was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and then recrystallized from hexane-ethyl acetate to obtain 0.25 g of ethyl 5-[1-methyl-1-(2-propynyloxy)ethyl]isoxazole-3-carboxylate.

Workup

  1. temperaturecooling
  2. extractionthe reaction mixture was extracted with methyl-t-butyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-b30784009ae44b17b2991405cf2f930f
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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