Benzyl Bromide → Methyl 3-(benzyloxy)isoxazole-5-carboxylate

HRID 705340Notes

Reaction equation

HRID 705340 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178498603HCID 178498603, compound

Product 1

HCID 5324203Methyl 3-(benzyloxy)isoxazole-5-carboxylateYield 59.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 3-hydroxyisoxazole-5-carboxylate (5.18 g, 36.2 mmol) was dissolved in acetone (90 mL) and treated with potassium carbonate (10.21 g, 73.8 mmol) at reflux for 1 hour. At that time, benzyl bromide (6.5 mL, 54.3 mmol) was added, and the mixture was heated at reflux for an additional 3 hours. The reaction mixture was removed from the oil bath and stirred at room temperature for 18 hours. The mixture was filtered and concentrated in vacuo leaving a yellow oil. The oil was purified by silica gel chromatography eluting with hexane/ethyl acetate (3:1) which gave the title compound as a light yellow solid (5.0 g, 59%).

Workup

  1. temperatureat reflux for 1 hour
  2. temperaturethe mixture was heated
  3. temperatureat reflux for an additional 3 hours
  4. customThe reaction mixture was removed from the oil bath
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated in vacuo
  7. customleaving a yellow oil
  8. customThe oil was purified by silica gel chromatography
  9. washeluting with hexane/ethyl acetate (3:1) which

Sources & evidence

ORD record
ord-27f619ea7dbf44d3b81e8d98087f59bf
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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