Triethylamine → 1-[3-(3-Chloro-phenyl)-isoxazol-5-yl]-ethanol

HRID 732055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732055
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](Cl)=[N:6][OH:7].[CH3:12][CH:13]([OH:16])[C:14]#[CH:15].C(N(CC)CC)C>C1C=CC=CC=1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[CH:15]=[C:14]([CH:13]([OH:16])[CH3:12])[O:7][N:6]=2)[CH:9]=[CH:10][CH:11]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 724759113-Chloro-benzohydroximoyl chloride

Produkt 1

HCID 670707661-[3-(3-Chloro-phenyl)-isoxazol-5-yl]-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Chloro-benzohydroximoyl chloride (e.g. Kim, Jae Nyoung; Ryu, Eung K; J. Org. Chem. (1992), 57(24), 6649-50) (2.84 g, 14.8 mmol) was suspended in benzene (50 ml) and cooled to 0° C. 3-Butyn-2-ol (2.10 g, 29.9 mmol) and triethylamine (1.89 ml, 26.7 mmol) were added. The mixture was heated to 60° C. for 1.5 houes, cooled and diluted with benzene and 1N aqueous hydrochloric acid. After stirring, the separated benzene layer was evaporated to dryness and the crude purified via flash chromatography over silica using heptane/ethyl acetate=5/1 giving after drying in vacuo the title compound (0.49 g, 15%). 1H NMR (CDCl3), δ (ppm): 1.64 (d, 3 H), 5.07 (dq, 1 H), 6.50 (s, 1 H), 7.40 (m, 2 H), 7.68 (m, 1 H), 7.79 (m, 1 H),

Aufarbeitung

  1. temperatureThe mixture was heated to 60° C. for 1.5 houes
  2. temperaturecooled
  3. customthe separated benzene layer was evaporated to dryness
  4. customthe crude purified via flash chromatography over silica
  5. dry with materialafter drying in vacuo the title compound (0.49 g, 15%)

Quellen und Nachweise

ORD-Eintrag
ord-f6dc243d6b7b468d8f740a9b7c9f0fff
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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