Isopropyl Acetate → HCID 69968236, compound

HRID 2289132Notes

Reaction equation

HRID 2289132 reaction equation
[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][C:10]([OH:15])=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][N:4]=1)[CH3:2].Br[C:17]([Br:20])([CH3:19])C.[C:21](=O)([O-])[O-].[Cs+].[Cs+].C(OC(C)C)(=O)C>CN(C=O)C>[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:21][CH2:19][CH2:17][Br:20])=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 7915Isopropyl AcetateHCID 10796Cesium carbonateHCID 116582,2-DibromopropaneHCID 135723525HCID 135723525, compound

Product 1

HCID 69968236HCID 69968236, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-ethyl-6-hydroxy-7-propylbenz[4,5]isoxazole (2.00 grams; 9.74 mmol) in dry DMF was treated with dibromopropane (7.17 mL; 38.97 mmol) and cesium carbonate (3.49 grams; 10.71 mmol). The solution was stirred at room temperature for 10 hours, then partioned between isopropyl acetate and pH 4.0 buffer. The organic layer was washed twice with water, dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography afforded the title compound (1.74 g).

Workup

  1. washThe organic layer was washed twice with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b7ff184146e44f58a563b737ef5d8b3
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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