Ethyl Acetate → 3-Bromo-5-(1-hydroxypropyl)isoxazole

HRID 1742527Notes

Reaction equation

HRID 1742527 reaction equation
C(OCC)(=O)C.C(=O)([O-])O.[K+].[CH:12]#[C:13][CH:14]([OH:17])[CH2:15][CH3:16].[Br:18][C:19](Br)=[N:20][OH:21]>O>[Br:18][C:19]1[CH:12]=[C:13]([CH:14]([OH:17])[CH2:15][CH3:16])[O:21][N:20]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 929811-Pentyn-3-olHCID 516893Potassium BicarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromide

Product 1

HCID 138020893-Bromo-5-(1-hydroxypropyl)isoxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Added to 800 ml of ethyl acetate were 8 ml of water, 60.0 g (0.6 mol) of potassium hydrogencarbonate and 73.5 g (0.88 mol) of 1-pentyn-3-ol. Under stirring, 40.5 g (0.2 mol) of dibromoformaldoxime were added at room temperature over 3 hours. After the resultant mixture was stirred at room temperature for 16 hours, water was added and the reaction product was extracted with ethyl acetate. Subsequent to concentration, 3-bromo-5-(1-hydroxypropyl) isoxazole was obtained as oil. It was distilled to collect a fraction at 97°-102° C./2 mmHg. Analytical results of the fraction obtained: Yield: 18 g (74%).

Workup

  1. extractionthe reaction product was extracted with ethyl acetate
  2. concentrationSubsequent to concentration

Sources & evidence

ORD record
ord-edefe859aa434f0686f16c779096feca
Source dataset
uspto-grants-1994_08
Patent number
US05338857

Reaction notes

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