Triethylamine → 5-[5-(5-Chloro-2-methoxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester

HRID 1616599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616599
C1(N=C=O)C=CC(N=C=O)=CC=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([C:22]#[CH:23])[CH:15]=1.[CH2:24]([O:26][C:27](=[O:36])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][N+:33]([O-])=[O:34])[CH3:25].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:24]([O:26][C:27](=[O:36])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:23]=[C:22]([C:16]2[CH:15]=[C:14]([Cl:13])[CH:19]=[CH:18][C:17]=2[O:20][CH3:21])[O:34][N:33]=1)[CH3:25]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 610091,4-DiisocyanatobenzeneHCID 13717120Ethyl 6-nitrohexanoateHCID 232607034-Chloro-2-ethynyl-1-methoxybenzene

Produkt 1

HCID 591677645-[5-(5-Chloro-2-methoxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl esterAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Add 1,4-phenylenediisocyanate (8.41 g, 52.5 mmol) to a stirred solution of 4-chloro-2-ethynyl-1-methoxy-benzene (4.0 g, 30.3 mmol) and 6-nitro-hexanoic acid ethyl ester (8.6 g, 45.4 mmol) in toluene (300 mL, anhydrous) and stir at room temperature under N2. Add triethylamine (7.3 mL, 52.5 mmol) and heat to reflux under N2 overnight. Filter mixture through a pad of Celite® and rinse with toluene. Concentrate to get 6.6 g of a orange oil. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-40% EtOAc/hexanes to afford the title compound (4.51 g, 76%). MS (IS) 338 (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-e510883347944519853b26d7757fc91b
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765796B2

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