Triethyloxonium tetrafluoroborate → Methyl 3-ethoxy-5-isoxazolecarboxylate

HRID 728380Notes

Reaction equation

HRID 728380 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.F[B-](F)(F)F.[CH2:16]([O+](CC)CC)[CH3:17]>C(Cl)Cl>[CH2:16]([O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1)[CH3:17]

Participants

4

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 178498603HCID 178498603, compound

Product 1

HCID 15007417Methyl 3-ethoxy-5-isoxazolecarboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred suspension of 3.53 g (24.67 mmole) of a commercial sample of methyl 3-hydroxy-5-isoxazolecarboxylate in 50 ml of methylene chloride was treated dropwise with a solution of triethyloxonium tetrafluoroborate (5.62 g, 29.60 mmole) dissolved in 30 ml of methylene chloride at room temperature. After stirring overnight the solution was washed with water (2×30 ml), 5% sodium bicarbonate (2×30 ml) and water once again. The organic layer was dried (magnesium sulfate) and evaporated in vacuo to furnish the title compound (3.61 g, 86% yield) as a light yellow solid, m.p. 77°-9° C. 1H-NMR (DMSO-d6)delta, 6.65 (1H, s), 3.93 (2H, q, J=7.4 Hz), 3.87 (3H, s) and 1.21 (3H, t, J=7.4 Hz); EIMS (m/z): 171 (M+, 48%), 56 (M+ --CH3, 4%), 143 (C5H 5 NO4, 31%), 112 (C4H2NO3, 12%) and 69 (C3H3NO, base); ir (potassium bromide): 3105, 1744, 1611, 1441, 1241, 1106, 974 and 797 cm-1.

Workup

  1. washwas washed with water (2×30 ml), 5% sodium bicarbonate (2×30 ml) and water once again
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-8aaf6f8f50824ed58662e9a794b304fb
Source dataset
uspto-grants-1991_09
Patent number
US05047554

Reaction notes

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