5-((Tert-butyldimethylsilyl)oxy)pentan-1-ol → 3-[6-(tert-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]hexyl]-2-chloropyridine

HRID 748719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748719
[Cl:1][C:2]1[C:7]([CH2:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[Si:19]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]O)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[Si:19]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:8]([C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:20])[CH3:21]

Komponenten

5

Edukt 3

HCID 36143185-((Tert-butyldimethylsilyl)oxy)pentan-1-olHCID 4622928CyanomethylenetributylphosphoraneHCID 230286692-Chloro-3-(4-chlorophenylsulfonylmethyl)pyridine

Produkt 1

HCID 597508833-[6-(tert-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]hexyl]-2-chloropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A toluene (5 ml) solution of the 2-chloro-3-(4-chlorophenylsulfonylmethyl)pyridine (200 mg, 0.662 mmol) obtained in Example 98, 5-(tert-butyldimethylsilyloxy)pentanol (288 mg, 1.32 mmol) and cyanomethylenetri-n-butylphosphorane (318 mg, 1.32 mmol) was heated under reflux for 22 hours under an argon atmosphere. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column, and the fraction obtained from the 15% ethyl acetate/hexane eluate was concentrated under reduced pressure, whereby the title compound (307 mg, 92%) was obtained as a colorless oil.

Aufarbeitung

  1. temperatureunder reflux for 22 hours under an argon atmosphere
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe fraction obtained from the 15% ethyl acetate/hexane eluate
  4. concentrationwas concentrated under reduced pressure, whereby the title compound (307 mg, 92%)
  5. customwas obtained as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-2dc6d845b92849e6b7f98b0734a08233
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399775B2

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