Sodium Hydroxide → Methyl 3-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylate

HRID 1773837

Reaktionsgleichung

Reaktionsgleichung von HRID 1773837
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13](=O)[CH:14]=[C:15]([C:20]2[CH:25]=[C:24]([Cl:26])[C:23]([F:27])=[C:22]([Cl:28])[CH:21]=2)[C:16]([F:19])([F:18])[F:17])=[C:8]2[CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4].[OH-:30].[Na+].[NH2:32]O.Cl>O.C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13]2[CH2:14][C:15]([C:20]3[CH:25]=[C:24]([Cl:26])[C:23]([F:27])=[C:22]([Cl:28])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:30][N:32]=2)=[C:8]2[CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 866937493-[3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester

Produkt 1

HCID 71472643Methyl 3-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylateAusbeute 50.384,102 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Stir a mixture of 3-[3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester (25 g, 53.6 mmol), NaOH (8.6 g, 0.214 mol) and NH2OH—HCl (7.4 g, 0.107 mmol) in water (100 mL) and THF (200 mL) at room temperature for overnight. After removal of the solvent under vacuum, the solution is diluted with water and extracted with EtOAc (200 mL×3). The combined organic layer is washed with brine, dried over anhydrous Na2SO4 and concentrated by vacuum to afford 3-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester as a white solid (26 g), which is used directly in the next step without purification. MS (m/z): 483 (M+1).

Aufarbeitung

  1. customAfter removal of the solvent under vacuum
  2. additionthe solution is diluted with water
  3. extractionextracted with EtOAc (200 mL×3)
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated by vacuum

Quellen und Nachweise

ORD-Eintrag
ord-afa90f93cb5b4911994e5f6ccc26c9df
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255111B2

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