1-Bromo-2-methylpropane → 3-Isobutoxy-5-methyl-isoxazole

HRID 1807533Notes

Reaction equation

HRID 1807533 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:15][CH:16]([CH3:18])[CH3:17]>CC(C)=O>[CH2:15]([O:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1)[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 24781Hymexazol

Product 1

HCID 666436343-Isobutoxy-5-methyl-isoxazoleYield 9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3-hydroxy-5-methylisoxazole (5.0 g, 50.5 mmol) in acetone (125 mL) at room temperature under argon was added K2CO3 (13.9 g, 101 mmol) and the reaction mixture was heated at 60° C. After 30 min, 1-bromo-2-methylpropane (10.4 g, 75.7 mmol) was added dropwise over 2 min. After 16 h the reaction mixture was cooled, filtered and concentrated. Purification by chromatography (silica, 70 to 100% ethyl acetate in heptane) gave the title compound (700 mg, 9%) as a volatile yellow liquid.

Workup

  1. temperatureAfter 16 h the reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification by chromatography (silica, 70 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-0dc5a8a04ccf46d09ae4c75d1a0ef23a
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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