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Synthesis 1986; 1986(8): 689-691
DOI: 10.1055/s-1986-31752
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Substitution at Secondary Benzylic Carbon with Aluminum Reagents: A Facile Synthesis of (±)-Naproxen

Tamejiro Hiyama* , Masuo Inoue
  • *Sagami Chemical Research Center, 4-1-1 Nishiohnuma, Sagamihara, Kanagawa 229, Japan
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Publication Date:
22 August 2002 (online)

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Cyanide substitution of 1-(6-methoxy-2-naphthyl)ethyl acetate with diethylaluminum cyanide takes place in good yields to give, after hydrolysis, 2-(6-methoxy-2-naphthyl)-propanoic acid. The aluminum-aided ethynyl substitution also proceeds efficiently.

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