Hydrochloric Acid → 4-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenoxy]-butan-1-ol

HRID 1891371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891371
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[Br:9][C:10]1[C:11]([Cl:32])=[CH:12][C:13](F)=[C:14]([S:16]([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([CH3:30])([CH3:29])[CH2:21][CH2:20]2)(=[O:18])=[O:17])[CH:15]=1.Cl>CN(C=O)C>[Br:9][C:10]1[C:11]([Cl:32])=[CH:12][C:13]([O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])=[C:14]([S:16]([N:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([CH3:30])([CH3:29])[CH2:21][CH2:20]2)(=[O:18])=[O:17])[CH:15]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 80641,4-ButanediolHCID 24758Sodium hydrideHCID 684692731-(5-Bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline

Produkt 1

HCID 684721504-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenoxy]-butan-1-olAusbeute 171 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 1,4-butanediol (0.44 mL, 5 mmole) in DMF (5 mL) at 0° C. was added sodium hydride (60%, 48 mg, 1.2 mmole) and the mixture stirred for 10 minutes. A solution of 1-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline (0.41 g, 1 mmole) in DMF (5 mL) was added. The mixture warmed to rt and was stirred for 1 hour. 1N hydrochloric acid solution (1 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and was dried over anhydrous MgSO4. Concentration of the filtrate provided a residue that was purified by silica gel chromatography [eluent: 40% ethyl acetate in hexane] to afford 4-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenoxy]-butan-1-ol as a light yellow foam (0.86 g). MS: 503.9 (M+H)+; tR=2.66 min (method 1).

Aufarbeitung

  1. stirringwas stirred for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialwas dried over anhydrous MgSO4
  5. customConcentration of the filtrate provided a residue that
  6. customwas purified by silica gel chromatography [eluent: 40% ethyl acetate in hexane]

Quellen und Nachweise

ORD-Eintrag
ord-062f058cb31b440bbea55cc328459345
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507536B2

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