1-Butynylbenzene → Methyl 4-ethyl-5-phenylisoxazole-3-carboxylate

HRID 1804459

Reaktionsgleichung

Reaktionsgleichung von HRID 1804459
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)#[C:2][CH2:3][CH3:4].[N+:11]([CH:14](C(OC)=O)[C:15]([O:17][CH3:18])=[O:16])([O-])=[O:12]>C1(C)C=C(C)C=C(C)C=1>[CH2:3]([C:2]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[N:11][O:12][C:1]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:4]

Komponenten

4

Edukt 2

HCID 693281-ButynylbenzeneHCID 226085Dimethyl nitromalonate

Produkt 1

HCID 58537177Methyl 4-ethyl-5-phenylisoxazole-3-carboxylateAusbeute 29,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7947MesityleneLösungsmittel

Versuchsvorschrift

A solution of but-1-ynylbenzene (404 mg, 3.11 mmol) and dimethyl nitromalonate (0.381 mL, 2.82 mmol) in mesitylene (5 mL) was heated to 150° C. for 24 h. The reaction mixture was concentrated, and the residue purified on silica gel column with hexanes/ethyl acetate (10/1) to afford methyl 4-ethyl-5-phenylisoxazole-3-carboxylate (194 mg). The compound had an HPLC ret. time=3.25 min.−Column. YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90% MeOH−10% water−0.2% H3PO; Start % B=0; Final % B=100. LC-MS: M+1=232+.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified on silica gel column with hexanes/ethyl acetate (10/1)

Quellen und Nachweise

ORD-Eintrag
ord-5ffdf350157d4ec5bf657e13e6e143a4
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354398B2

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