Potassium Carbonate → 3-Bromo-5-[(2S)-oxiran-2-yl]isoxazole

HRID 1794777Notes

Reaction equation

HRID 1794777 reaction equation
Br[CH2:2][C@@H:3]([C:5]1[O:9][N:8]=[C:7]([Br:10])[CH:6]=1)[OH:4].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:10][C:7]1[CH:6]=[C:5]([C@@H:3]2[CH2:2][O:4]2)[O:9][N:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 13626979HCID 13626979, compound

Product 1

HCID 865845593-Bromo-5-[(2S)-oxiran-2-yl]isoxazoleYield 76.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (1R)-2-bromo-1-(3-bromoisoxazole-5-yl)ethanol (which was obtained in Example 119) (1.44 g, 5.31 mmol), potassium carbonate (1.46 g, 10.62 mmol) and acetone (30 mL) was stirred at ambient temperature for 48 hours. The reaction mixture was filtered, and the solvent was removed in vacuo. The residue was purified by flash chromatography (hexanes/chloroform/isopropyl alcohol 8/1.8/0.2) to give a colorless oil (0.774 g, 53% yield); 1H NMR (300 MHz, CDCl3) δ 3.17 (m, 1H), 3.21 (m, 1H), 3.99 (m, 1H), 6.38 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by flash chromatography (hexanes/chloroform/isopropyl alcohol 8/1.8/0.2)

Sources & evidence

ORD record
ord-592c3ca1134849f99c5037f5a528820c
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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