Reaktion #66327

Reaktionsgleichung

1′-trifluoroacetyl-spiro[3,4-dihydrobenzopyran-2,4′-piperidine]

propanoyl chloride

Tin tetrachloride

→

1′-trifluoroacetyl-6-(propanoyl)-spiro[3,4-dihydrobenzopyran-2,4′-piperidine]

Ausbeute 81.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethen quenched with aqueous 2N HCl at 0° C
2. 2
   ExtraktionThe aqueous layer was extracted twice with methylene chloride
3. 3
   Waschenthe combined organics was washed with brine
4. 4
   Trocknendried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto provide a crude product
8. 8
   SonstigeThe crude product was purified by ISCO (80 g column) chromatography

Vorschrift

A mixture of 1′-trifluoroacetyl-spiro[3,4-dihydrobenzopyran-2,4′-piperidine] (1.49 g, 4.98 mmol) and propanoyl chloride (0.4 mL, 5 mmol) in methylene chloride (13 mL) was cooled at 10° C. Tin tetrachloride (1M solution in methylene chloride) (0.76 mL, 6.5 mmol) was added at 10° C. and stirred at 10° C. for 20 min then quenched with aqueous 2N HCl at 0° C. The aqueous layer was extracted twice with methylene chloride and the combined organics was washed with brine, dried (Na2SO4), filtered, and concentrated to provide a crude product. The crude product was purified by ISCO (80 g column) chromatography using 17 to 35% EtOAc in hexane to produce 1′-trifluoroacetyl-6-(propanoyl)-spiro[3,4-dihydrobenzopyran-2,4′-piperidine] (1.42 g, 81%),

Quelle