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

HRID 1061272Notes

Reaction equation

HRID 1061272 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-754d61f2797a42c2bd63e8a30f4c8934
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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