Triethylamine → Ethyl 5-(morpholinomethyl)isoxazole-3-carboxylate

HRID 872782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 872782
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[CH2:10]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[C:11]#[CH:12].C(N(CC)CC)C>C1(C)C=CC=CC=1.O>[O:16]1[CH2:17][CH2:18][N:13]([CH2:10][C:11]2[O:8][N:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:12]=2)[CH2:14][CH2:15]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 4129414-(2-Propyn-1-yl)morpholineHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

Produkt 1

HCID 23006302Ethyl 5-(morpholinomethyl)isoxazole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To the solution of ethyl chlorooximidoacetate (0.588 g, 3.88 mmol) and 4-(prop-2-ynyl)morpholine (0.971 g, 7.76 mmol) in toluene (5 mL) was added solution of triethylamine (0.54 mL, 3.88 mmol) in toluene (5 mL) dropwise. The resultant mixture was stirred at RT for 5 h. After the completion of the reaction as evidenced by LC-MS, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic solvent was then dried over anhydrous sodium sulfate and evaporated. The crude product was purified by Combiflash (Heptane:EtOAc eluent). Yield 0.2 g. 1H NMR (400 MHz; MeOD): δ 1.38 (t, 3H), 2.53 (m, 4H), 3.69 (m, 4H), 3.78 (d, 2H), 4.41 (q, 2H), 6.73 (m, 1H).

Aufarbeitung

  1. customAfter the completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic solvent was then dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe crude product was purified by Combiflash (Heptane:EtOAc eluent)

Quellen und Nachweise

ORD-Eintrag
ord-7308ad297900412db1a4865e1737e70c
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975254B2

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