Triethylamine → 4-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-butyric acid methyl ester

HRID 1443721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1443721
C1(N=C=O)C=CC(N=C=O)=CC=1.[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])#[CH:14].[CH3:23][O:24][C:25](=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][N+:30]([O-])=[O:31].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25](=[O:33])[CH2:26][CH2:27][CH2:28][C:29]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])[O:31][N:30]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 610091,4-DiisocyanatobenzeneHCID 543911Methyl 5-nitropentanoateHCID 5829121-Ethynyl-2-methoxybenzene

Produkt 1

HCID 591677844-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-butyric acid methyl esterAusbeute 112,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Add 1,4-phenylenediisocyanate (19.22 g, 120.0 mmol) to a stirred solution of 1-ethynyl-2-methoxy-benzene (2204901, 5.29 g, 40.0 mmol) and 5-nitro-pentanoic acid methyl ester (7.91 g, 49.1 mmol) in toluene (300 mL, anhydrous) and stir under N2. Add triethylamine (16.7 mL, 120.0 mmol) and heat to reflux under N2 overnight. Filter mixture through a pad of Celite® and rinse with toluene. Concentrate to get 12.4 g yellow oil. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-30% EtOAc/hexanes to afford the title compound (14.0 g, 74%). MS (IS) 276 (M+1)+.

Aufarbeitung

  1. temperatureto reflux under N2 overnight
  2. filtrationFilter mixture through a pad of Celite®
  3. washrinse with toluene
  4. concentrationConcentrate

Quellen und Nachweise

ORD-Eintrag
ord-3439333d0c9b45aaaac5c4ab14b92823
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662771B2

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