Bis(1,3-dichloroisopropyl ether) → 4-[1-(4-Methylphenylsulfonyl)piperidin-4-yl]benzaldehyde

HRID 1388014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1388014
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC[CH:25]([O:28]C(CCl)CCl)CCl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:25]=[O:28])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 93323Bis(1,3-dichloroisopropyl ether)HCID 41684661-[(4-Methylphenyl)sulfonyl]-4-phenylpiperidine

Produkt 1

HCID 184726214-[1-(4-Methylphenylsulfonyl)piperidin-4-yl]benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(4-methylphenylsulfonyl)-4-phenylpiperidine (1.0 g) and 1,1-dichloromethylmethylether (0.57 ml) in dichloromethane (5 ml) was added at 0° C. a solution of titanium tetrachloride (0.7 ml) in dichloromethane (5 ml), and the mixture was stirred at room temperature for 2 hours. The mixture was added to stirred ice/water to stop the reaction. The mixture was extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate solution and saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/hexane=1:4→1:2) to give pale yellow crystals of 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]benzaldehyde (0.381 g). (469.4 mg of the starting materials were collected)

Aufarbeitung

  1. additionThe mixture was added
  2. customthe reaction
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with sodium bicarbonate solution and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationUnder reduced pressure, the mixture was concentrated
  7. customthe residue was purified with column chromatography (ethyl acetate/hexane=1:4→1:2)

Quellen und Nachweise

ORD-Eintrag
ord-f317f95a01b24f75a4263122498e796d
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268354B1

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