Tetrabutylammonium Fluoride → 6-(4-Chlorophenylsulfonyl)-6-(2-chloropyridin-3-yl)-1-hexanol

HRID 748720Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748720
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]([C:43]1[C:44]([Cl:49])=[N:45][CH:46]=[CH:47][CH:48]=1)[S:33]([C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)(=[O:35])=[O:34])(C(C)(C)C)(C)C>O1CCCC1>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([S:33]([CH:32]([C:43]2[C:44]([Cl:49])=[N:45][CH:46]=[CH:47][CH:48]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][OH:26])(=[O:35])=[O:34])=[CH:37][CH:38]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 597508833-[6-(tert-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]hexyl]-2-chloropyridine

Produkt 1

HCID 230288406-(4-Chlorophenylsulfonyl)-6-(2-chloropyridin-3-yl)-1-hexanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under ice cooling, tetrabutylammonium fluoride (a 1 mol/l tetrahydrofuran solution; 0.70 ml) was added to a tetrahydrofuran (10 ml) solution of 3-[6-(tert-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]hexyl]-2-chloropyridine (294 mg, 0.585 mmol). The resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed successively with water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column. The fraction obtained from the hexane:ethyl acetate (=1:1) eluate was concentrated under reduced pressure, whereby the title compound (212 mg, 93%) was obtained as a colorless oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe mixture was washed successively with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe fraction obtained from the hexane
  8. concentrationethyl acetate (=1:1) eluate was concentrated under reduced pressure, whereby the title compound (212 mg, 93%)
  9. customwas obtained as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-1e4e494417244254813c794458fb2123
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399775B2

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