Synthesis of 1-aryl-1-phenylpropenes using an alkylation-rearrangement-methylation-isomerization one-pot reaction sequence |
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Authors: | Nenad Mara? Franc Perdih Marijan Ko?evar |
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Institution: | (1) Sphinx Pharmaceuticals, A Division of Eli Lilly and Company, 840 Memorial Drive, Cambridge, MA, 02139, U.S.A;(2) Mobil Technology Company–Strategic Research Center, Paulsboro, NJ, 08066, U.S.A |
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Abstract: | (Z/E)-1-(2-Methoxyaryl)-1-phenylpropenes have been prepared in good yields by heating a mixture of a phenolic substrate, cinnamyl
chloride, tetramethylammonium chloride and K2CO3 in polyethyleneglycol at 180°C. The one-pot synthesis proceeds through four discrete reaction steps: alkylation of the
phenol with cinnamyl chloride, Claisen rearrangement, O-methylation and double-bond migration. The configuration of one crystalline product was determined using a single-crystal
X-ray diffraction analysis. The thermodynamic and structural features of the products were evaluated using computational chemistry
techniques.
![MediaObjects/11532_2011_74_Fig1_HTML.jpg](/content/2T8268G34771172J/MediaObjects/11532_2011_74_Fig1_HTML.jpg) |
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