Hydrogen Bromide → 7-[2-(N-Dodecyl-N-methylamino)ethoxy]-3,4dihydro-2-(trifluoromethyl)-2H-1-benzopyran-2-ol

HRID 1383903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383903
[CH2:1]([N:13]([CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])=[C:20]([O:32]C)[CH:19]=1)[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Br>O>[CH2:1]([N:13]([CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]2[CH2:24][CH2:25][C:26]([C:27]([F:30])([F:29])[F:28])([OH:31])[O:32][C:20]=2[CH:19]=1)[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 183190324-[4-[2-(N-Dodecyl-N-methylamino)ethoxy]-2-methoxyphenyl]-1,1,1-trifluoro-2-butanone

Produkt 1

HCID 211888567-[2-(N-Dodecyl-N-methylamino)ethoxy]-3,4dihydro-2-(trifluoromethyl)-2H-1-benzopyran-2-olAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-[4-[2-(N-dodecyl-N-methylamino)ethoxy]-2-methoxyphenyl]-1,1,1-trifluoro-2-butanone (157 mg, 0.33 mmol) and hydrobromic acid (47%, 3 ml) was refluxed for 3.5 h. After cooling to r.t., the mixture was diluted with water, extracted with dichloromethane. The organic layer was washed with sat. sodium bicarbonate, brine, dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (ethyl acetate/acetone 3:1) to afford the title compound (60 mg, 40%) as a clear oil.

Aufarbeitung

  1. temperaturewas refluxed for 3.5 h
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with sat. sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel (ethyl acetate/acetone 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-520c9a1e3c7747cfb54745ab0547959a
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255496B1

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