Dimethyl nitromalonate → Methyl 4-isopropyl-5-(pyridin-2-yl)isoxazole-3-carboxylate

HRID 1951945

Reaktionsgleichung

Reaktionsgleichung von HRID 1951945
[CH3:1][CH:2]([CH3:11])[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[N+:12]([CH:15](C(OC)=O)[C:16]([O:18][CH3:19])=[O:17])([O-])=[O:13].F[P-](F)(F)(F)(F)F.C([N+]1C=CN(C)C=1)CCC>C1(C)C=CC=CC=1>[CH:2]([C:3]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[N:12][O:13][C:4]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)([CH3:11])[CH3:1]

Komponenten

5

Edukt 3

HCID 226085Dimethyl nitromalonateHCID 27341741-Butyl-3-methylimidazolium hexafluorophosphateHCID 20771880(3-Methylbut-1-ynyl)pyridine

Produkt 1

HCID 58062818Methyl 4-isopropyl-5-(pyridin-2-yl)isoxazole-3-carboxylateAusbeute 2,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of (3-methylbut-1-ynyl)pyridine (170 mg, 1.17 mmol), dimethyl nitromalonate (0.395 mL, 2.93 mmol), and 1-butyl-3-methylimidazolium hexafluorophosphate (0.024 mL, 0.117 mmol) in toluene (7 mL) was heated to 170° C. for 120 minutes under microwave. The reaction mixture was concentrated and purified by silica gel chromatography with hexanes/ethyl acetate (10/1) to afford methyl 4-isopropyl-5-(pyridin-2-yl)isoxazole-3-carboxylate (11 mg, 0.033 mmol, 2.8% yield). The compound had an HPLC retention time=2.96 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% H3PO4; Start % B=0; Final % B=100. LC-MS: M+1=247.15. 1H NMR (400 MHz, CDCl3) δ ppm 1.36 (s, 3H), 1.38 (s, 3H), 4.02 (s, 3H), 4.03-4.10 (m, 1H), 7.33-7.38 (m, 1H), 7.80-7.90 (m, 2H), and 8.72-8.76 (m, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel chromatography with hexanes/ethyl acetate (10/1)

Quellen und Nachweise

ORD-Eintrag
ord-94408d240d934dd6a45082f9050437b7
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404672B2

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