Reaktion #479620

Reaktionsgleichung

potassium bis(trimethylsilyl)amide

Benzyltriphenylphosphonium bromide

N-(3-formyl-phenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine

→

title compound

N-(3-(2-Phenylvinyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at ambient temperature for 2 h
2. 2
   SonstigeEvaporation and chromatography on silica-gel
3. 3
   Wascheneluting with toluene-EtOAc

Vorschrift

Benzyltriphenylphosphonium bromide (0.765 g, 1.77 mmol) was dispersed into THF (12 ml) and cooled at 0° C. To the cooled suspension was added dropwise a solution of potassium bis(trimethylsilyl)amide (0.5 M, 3.5 ml, 1.75 mmol). After stirring at 0° C. for 1 h, a solution of). N-(3-formyl-phenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.304 g, 1.0 mmol) in THF was added. The reaction mixture was stirred at ambient temperature for 2 h. Evaporation and chromatography on silica-gel eluting with toluene-EtOAc to give the title compound. 1H NMR: 8.48 (d,1H,J=3.4 Hz), 8.30 (d,1H,J=2.0 Hz), 7.65 (d,1H,J=7.8 Hz), 7.30-6.74 (m,8H), 6.60 (q,2H,J=12.2, 37.1 Hz), 4.68 (s,2H), 2.87 (q,2H,J=7.3 Hz), 1.28 (t,3H,J=7.4 Hz). MS calcd 378.1; MS (M+1) 379.1.

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