Hydrochloric Acid → 5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid

HRID 2167007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2167007
[Li+].[OH-].C([O:5][C:6]([C:8]1[S:9][C:10]([C:14]2[CH2:18][C:17]([C:23]3[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=3)([C:19]([F:22])([F:21])[F:20])[O:16][N:15]=2)=[CH:11][C:12]=1[CH3:13])=[O:7])C.Cl>C1COCC1.O>[Cl:30][C:25]1[CH:24]=[C:23]([C:17]2([C:19]([F:20])([F:22])[F:21])[O:16][N:15]=[C:14]([C:10]3[S:9][C:8]([C:6]([OH:7])=[O:5])=[C:12]([CH3:13])[CH:11]=3)[CH2:18]2)[CH:28]=[C:27]([Cl:29])[CH:26]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium Hydroxide2×HCID 665872885-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid ethyl ester

Produkt 1

HCID 674288635-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acidAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

LiOH (3.2 g) is added to a solution of 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid ethyl ester (9.88 g) in a mixture of THF and water (240 ml, 9:1). After 16 hours at room temperature, LiOH (1.05 g) and THF (150 ml) was added. The reaction mixture was heated at 50° C. for 10 hours. HCl (2N) was added to the reaction mixture until pH 1-2 was obtained. The mixture was then extracted three times with ethyl acetate. The organic phases were combined, washed with water and a saturated aqueous solution of NaCl, dried over Na2SO4 and concentrated in vacuo to yield 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-3-methyl-thiophene-2-carboxylic acid (9.3 g) as brown resin. The crude product is used without further purification.

Aufarbeitung

  1. customwas obtained
  2. extractionThe mixture was then extracted three times with ethyl acetate
  3. washwashed with water
  4. dry with materiala saturated aqueous solution of NaCl, dried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5cc6d25c4ea14db9a365705d5ac61f2a
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09044389B2

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