Aromatic Benzhydrylation: Part III - Synthesis of Chromones of Triphenylmethane Type
2-O-Methylphloroacetophenone (1) when treated with diphenylcarbinol in the presence of boron trifluoride etherate and dioxan gives a mixture of 3-C-benzhydryl-(4a), 5-C-benzhydryl-(3a) and 3,5-di-C-benzhydryl-(2a) derivatives in 19.7, 14.8 and 6.7percent yields respectively.Location of benzhydryl unit in 3a and 4a has been made (i) by NOE studies and (ii) by converting them into 7d and 8d respectively via 3b and 4b and comparing them with authentic 7d and 8d prepared by benzhydrylation of 5,7-dihydroxychromone (5) followed by methylation of the products (7a and 8a).Locationof benzhydryl unit in 7a and 8a can be made by comparing the PMR spectra of their methyl ethers and acetates
Jain, A. C.,Gupta, S. M.,Bambah, Pawan
p. 393 - 397
(2007/10/02)
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