Journal of Pharmaceutical Sciences p. 863 - 865 (1983)
Update date:2022-07-29
Topics:
Chen
Nelson
1,1-Diethoxy-3-(1-naphthoxy)-3-propanol (V), the diethyl acetal of an important aldehyde intermediate in the metabolic N-dealkylation of propranolol, was prepared from compound X, the product of the reaction of the lithium salt of methyl methylsulfinylmethyl sulfide with 2-(1-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[1,2-b]lpyrans VI and VII. Compounds VI and VII were characterized on the basis of mass spectral and 1H- and 13C-NMR data. The stereochemistry of these compounds was assigned on the basis of the 300-MHz 1H-NMR spectra of the acetate esters (XI and XII).
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Doi:10.1021/om034289f
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(1999)Doi:10.1021/jo00345a052
(1982)Doi:10.1016/j.tet.2004.10.059
(2005)Doi:10.1021/jo00327a028
(1981)Doi:10.1002/ardp.19823150606
(1982)