Pyridine → 3,3-Bis(4-fluorophenyl)propanal

HRID 2190302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190302
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.N1C=CC=CC=1>CS(C)=O.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[CH2:9][CH:10]=[O:11])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 8471TriethylamineHCID 197832883,3-Bis(4-fluorophenyl)propanol

Produkt 1

HCID 183626473,3-Bis(4-fluorophenyl)propanal

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 3,3-bis(4-fluorophenyl)propan-1-ol, prepared in the previous step, in DMSO (100 mL) at room temperature was added triethylamine (13.1 g, 129 mmol, 18 mL) and SO3.pyridine (4.52 g, 28.4 mmol). The reaction mixture was stirred at room temperature for 30 min, diluted with Et2O, washed with water (1×), saturated NH4Cl (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 5% to 40% EtOAc in hexanes) gave 3,3-bis(4-fluorophenyl)propanal.

Aufarbeitung

  1. washwashed with water (1×), saturated NH4Cl (1×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (eluted with 5% to 40% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fc3bf366b6b24be9bff7f08f36df4394
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324396B2

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