Add time:08/13/2019         Source:sciencedirect.com

□ 1,1-Diethoxy-3-(1-naphthoxy)-2-propanol (V), the diethyl acetal of an important aldehyde intermediate in the metabolic N-deal-kylation of propranolol, was prepared from compound X, the product of the reaction of the lithium salt of methyl methylsulfinylmethyl sulfide with 2-(l-naphthoxy)-acetaldehyde. Compound X, as a mixture of three diastereomeric α-hydroxydithioacetal derivatives, when treated with ethyl orthoformate afforded the desired acetal V as well as two ring-closure products, the dihydronaphtho[l,2-b]pyrans VI and VII. Compounds VI and VII were characterized on the basis of mass spectral and 1H- and I3C-NMR data. The stereochemistry of these compounds was assigned on the basis of the 300-MHz 1H-NMR spectra of their acetate esters (XI and XII).

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