Triethylamine → Ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate

HRID 1795025

Reaktionsgleichung

Reaktionsgleichung von HRID 1795025
[CH2:1]([O:3][C:4](=[O:9])[C:5](Cl)=[N:6][OH:7])[CH3:2].[F:10][C:11]([F:21])([F:20])[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[CH2:17])=[CH:14][CH:13]=1.C(N(CC)CC)C>O1CCCC1>[F:10][C:11]([F:20])([F:21])[C:12]1[CH:13]=[CH:14][C:15]([CH:16]2[O:7][N:6]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:9])[CH2:17]2)=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27827981-Ethenyl-4-(trifluoromethyl)benzeneHCID 6816376Ethyl chloro(hydroximino)acetate

Produkt 1

HCID 22064077Ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylateAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred mixture of 2-chloro-2-hydroxyiminoacetic acid ethyl ester (2.11 g, 13.52 mmol) and 4-trifluoromethystyrene (2.0 g, 11.27 mmol) in anhydrous tetrahydrofuran (15 ml) was added dropwise a solution of triethylamine (3.0 ml, 21.52 mmol) in tetrahydrofuran (5 ml) at room temperature. The resulting reaction mixture was stirred at an atmosphere of nitrogen for 16 hours, filtered, partitioned between water and ethyl acetate (2×50 ml), washed with saturated aqueous sodium bicarbonate, 30% aqueous ammonium chloride, brine, dried over sodium sulfate, and concentrated to afford a pale yellow solid, which was purified by chromatography (2:8 EtOAc:Hexane) to afford ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate (2.86 g, M+1=288.2)

Aufarbeitung

  1. customThe resulting reaction mixture
  2. filtrationfiltered
  3. custompartitioned between water and ethyl acetate (2×50 ml)
  4. washwashed with saturated aqueous sodium bicarbonate, 30% aqueous ammonium chloride, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto afford a pale yellow solid, which
  8. customwas purified by chromatography (2:8 EtOAc:Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-113f9c1f7be64082b02382b2c3f7e41a
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026321B2

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