Reaktionsgleichung
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](/[CH:18]=[CH:19]/[CH2:20][C@@H:21]([OH:23])[CH3:22])[CH:13]=1.C([O-])(O)=O.[Na+]>C(N(CC)CC)C>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:23][C@H:21]([CH2:20]/[CH:19]=[CH:18]/[C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)[CH3:22])(=[O:9])=[O:8])=[CH:3][CH:2]=1Komponenten
5
Versuchsvorschrift
Under a nitrogen atmosphere, p-toluenesulfonyl chloride (7.01 g, 36.77 mmol) was added to a stirring solution of (2S)-(4E)-5-(3-pyridyl)-4-penten-2-ol (3.00 g, 18.38 mmol) in dry triethylamine (20 mL) at 0° C. After stirring and warning to ambient temperature over 18 h, the mixture was stirred with cold, saturated NaHCO3 solution (50 mL) for 1 hour and extracted with chloroform (3×50 mL). The combined chloroform extracts were dried (K2CO3), filtered, and concentrated by rotary evaporation to afford a thick, dark-brown mass (˜7 g). The crude product was purified by column chromatography on silica gel, eluting with chloroform-acetone (98:2, v/v) to afford 4.00 g (68.6%) of a light-brown syrup.
Aufarbeitung
- extractionextracted with chloroform (3×50 mL)
- dry with materialThe combined chloroform extracts were dried (K2CO3)
- filtrationfiltered
- concentrationconcentrated by rotary evaporation
- customto afford a thick, dark-brown mass (˜7 g)
- customThe crude product was purified by column chromatography on silica gel
- washeluting with chloroform-acetone (98:2
Quellen und Nachweise
- ORD-Eintrag
- ord-31d6d19e69274736a64ad8b256a2e8fe
- Quelldatensatz
- uspto-grants-2010_09
- Patentnummer
- US07790757B2
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