Triethylamine → HCID 67168649, Verbindung

HRID 1506317

Reaktionsgleichung

Reaktionsgleichung von HRID 1506317
[C:1]([C:3]1([CH3:6])[CH2:5][CH2:4]1)#[CH:2].Cl/[C:8](=[N:14]\[OH:15])/[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(N(CC)CC)C>C(OCC)C>[CH2:12]([O:11][C:9]([C:8]1[CH:2]=[C:1]([C:3]2([CH3:6])[CH2:5][CH2:4]2)[O:15][N:14]=1)=[O:10])[CH3:13]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 95760052-Chloro-2-hydroxyiminoacetic acid ethyl esterHCID 215905601-Ethynyl-1-methylcyclopropane

Produkt 1

HCID 67168649HCID 67168649, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a mixture of 1-ethynyl-1-methylcyclopropane (Preparation 4B, 5.0 g, 62.4 mmol) and (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (4.73 g, 31.2 mmol) in diethyl ether (80 mL) was added a solution of triethylamine (8.67 mL, 62.4 mmol) in diethyl ether (20 mL) dropwise over 75 min. After complete addition, the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by flash silica gel chromatography using a 10% mixture of ethyl acetate in hexane to give ethyl-5-(1-methylcyclopropyl)isoxazole-3-carboxylate (3.54 g, 65% yield) as a yellow liquid. The product had an HPLC ret. time=2.23 min.-(condition B); LC/MS M+1=196.07. 1H NMR (400 MHz, CDCl3) δ ppm 0.79 (m, 2H), 1.13 (m, 2H), 1.26 (t, J=7.15 Hz, 3H), 1.35 (s, 3H), 4.31 (q, J=7.12 Hz, 2H), and 6.23 (s, 1H).

Aufarbeitung

  1. additionAfter complete addition
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by flash silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d720e293ef4a49239d4156d3db03cc95
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216972B2

Verknüpfte Notizen

Wird geladen…