Water → 3-(Azidomethyl)-5-methyl-1,2-oxazole

HRID 2119980Notes

Reaction equation

HRID 2119980 reaction equation
Br[CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1.[N-:9]=[N+:10]=[N-:11].[Na+].O>CC(C)=O>[N:9]([CH2:2][C:3]1[CH:7]=[C:6]([CH3:8])[O:5][N:4]=1)=[N+:10]=[N-:11]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 27763043-(Bromomethyl)-5-methylisoxazole

Product 1

HCID 234409373-(Azidomethyl)-5-methyl-1,2-oxazoleYield 242.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the 3-bromomethyl-5-methyl-isoxazole (150 mg, 0.9 mmol) in acetone (1 mL) was added NaN3 (166 mg, 0.26 mmol) at rt. The reaction mixture was then stirred for 48 h. Then, the reaction mixture was poured into water (10 mL) and extracted with EtOAc (3×10 mL) dried and evaporated. The product was chromatographed on silica gel eluting with EtOAc/hexane 1:1 to leave the title compound as a colorless liquid (87 mg, 74%). m/z 138.0 (M).

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. customdried
  3. customevaporated
  4. customThe product was chromatographed on silica gel eluting with EtOAc/hexane 1:1

Sources & evidence

ORD record
ord-0654f9e3377149beb4037a60a18fa66d
Source dataset
uspto-grants-2004_02
Patent number
US06686352B2

Reaction notes

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