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Volumn 36, Issue 1, 2007, Pages 38-39

Iron(III) chloride-catalyzed reductive etherification of carbonyl compounds with alcohols

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EID: 34247184762     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.38     Document Type: Article
Times cited : (40)

References (24)
  • 20
    • 34247266685 scopus 로고    scopus 로고
    • 2 (56%), THF (0%).
    • 2 (56%), THF (0%).
  • 21
    • 0030863986 scopus 로고    scopus 로고
    • 3): M. Node, K. Nishide, Y. Shigeta, K. Obata, H. Shiraki, H. Kunishige, Tetrahedron 1997, 53, 12883.)
    • 3): M. Node, K. Nishide, Y. Shigeta, K. Obata, H. Shiraki, H. Kunishige, Tetrahedron 1997, 53, 12883.)
  • 24
    • 34247275879 scopus 로고    scopus 로고
    • Typical procedure: To a suspension of anhydrous iron(III) chloride (2.4 mg, 0.015 mmol) and benzaldehyde (30 μL, 0.30 mmol) in nitromethane (1.5 mL) was added 3-phenylpropanol (49.1 mg, 0.36 mmol) and triethylsilane (58 μL, 0.36 mmol) successively at room temperature under an argon atmosphere. After stirring for 1 h, the reaction mixture was quenched with a phosphate buffer (pH 7, 20 mL). The organic materials were extracted with dichloromethane, washed with brine, and dried over sodium sulfate. 1-Benzyloxy-3-phenylpropane (64.9 mg, 97%) was isolated by thin-layer chromatography on silica gel.
    • Typical procedure: To a suspension of anhydrous iron(III) chloride (2.4 mg, 0.015 mmol) and benzaldehyde (30 μL, 0.30 mmol) in nitromethane (1.5 mL) was added 3-phenylpropanol (49.1 mg, 0.36 mmol) and triethylsilane (58 μL, 0.36 mmol) successively at room temperature under an argon atmosphere. After stirring for 1 h, the reaction mixture was quenched with a phosphate buffer (pH 7, 20 mL). The organic materials were extracted with dichloromethane, washed with brine, and dried over sodium sulfate. 1-Benzyloxy-3-phenylpropane (64.9 mg, 97%) was isolated by thin-layer chromatography on silica gel.


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