Reaktion #1100593

Reaktionsgleichung

Potassium bis(trimethylsilyl)amide

product

5-(1-Phenyl-ethyl)-4,5,6,6a-tetrahydro-3bH-1-thia-5-azacyclopenta[α]-pentalen-7-one

→

subtitle compound

Ausbeute 74.8%

7-Methylene-5-(1-phenyl-ethyl)-3b,4,5,6,6a,7-hexahydro-1-thia-5-aza-cyclopenta[α]pentalene

Ausbeute 74.8%

Lösungsmittel

THF

dichloromethane

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   workup.WAITto come to room temperature over 1 hour
3. 3
   Waschenwas washed with brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated to an oil
6. 6
   SonstigeThe crude was purified by column chromatography (SiO2)

Vorschrift

Potassium bis(trimethylsilyl)amide (308 mg, 1.55 mmol) was added to a solution of methyl triphenylphosphonium bromide (575 mg, 1.61 mmol) in 7 mL of THF at 0° C. After 30 minutes of stirring at 0° C., the product from step e) (303 mg, 1.07 mmol) dissolved in 2 mL of THF was added to the reaction mixture and was allowed to come to room temperature over 1 hour. The reaction mixture was diluted with dichloromethane (30 mL) and was washed with brine, dried (MgSO4) and concentrated to an oil. The crude was purified by column chromatography (SiO2) using 5-55% ethylacetate-hexane gradient to afford the subtitle compound (226 mg, yield: 74.8%). MS calculated for C18H19NS +H: 282, observed: 282.

Quelle