Boron trifluoride etherate → Methyl 5-methyl-3-isoxazolepropanoate

HRID 544626Notes

Reaction equation

HRID 544626 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])[CH:3]=1.B(F)(F)F.[CH3:16]COCC>CO>[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][CH2:8][C:9]([O:11][CH3:16])=[O:10])[CH:3]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 1333605-Methyl-3-isoxazolepropionic acid

Product 1

HCID 573461Methyl 5-methyl-3-isoxazolepropanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 75.4 g of 5-methyl-3-isoxazolepropanoic acid, 150 ml of boron trifluoride etherate and 400 ml of methanol was heated at reflux for eight hours. The reaction mixture was concentrated in vacuo, made basic with sodium bicarbonate solution and extracted with methylene dichloride. The extracts were concentrated in vacuo and the residue distilled at 90°-100° C.(0.05 mm) to give 73 g of methyl 5-methyl-3-isoxazolepropanoate which crystallized to a solid, m.p. 54°-55° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for eight hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. extractionextracted with methylene dichloride
  5. concentrationThe extracts were concentrated in vacuo
  6. distillationthe residue distilled at 90°-100° C.(0.05 mm)

Sources & evidence

ORD record
ord-e5dd0da2bd0e448486dea7865bd88024
Source dataset
uspto-grants-1984_05
Patent number
US04451476

Reaction notes

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