Water → 1-[2,4-Bis(trifluoromethyl)benzyl]azepane-4-carbaldehyde

HRID 1620562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620562
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:4]=1[CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][OH:14])[CH2:8][CH2:7]1.C(N(CC)CC)C.O>CS(C)=O>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:4]=1[CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][CH:9]([CH:13]=[O:14])[CH2:8][CH2:7]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 8471TriethylamineHCID 86678740{1-[2,4-Bis(trifluoromethyl)benzyl]azepan-4-yl}methanol

Produkt 1

HCID 866787411-[2,4-Bis(trifluoromethyl)benzyl]azepane-4-carbaldehydeAusbeute 32,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of {1-[2,4-bis(trifluoromethyl)benzyl]azepan-4-yl}methanol (901.4 mg) and triethylamine (1.06 mL) in DMSO (1.01 mL) was added sulfur trioxide pyridine complex (1.21 g). The reaction mixture was stirred at room temperature for 1.5 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (289.8 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-00f6bd9b319d4c2b8162a014d8f40543
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772277B2

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