Chen C H, Nelson W L
J Pharm Sci. 1983 Aug;72(8):863-5. doi: 10.1002/jps.2600720807.
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-(1-naphthoxy)-acetaldehyde. Compound X, as a mixture of three diastereomeric alpha-hydroxydithioacetal derivatives, when treated with ethyl orthoformate afforded the desired acetal V as well as two ring-closure products, the dihydronaphtho[1,2-b]pyrans 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 their acetate esters (XI and XII).
1,1 - 二乙氧基 - 3 - (1 - 萘氧基) - 2 - 丙醇（V）是普萘洛尔代谢N - 去烷基化过程中一种重要醛中间体的二乙缩醛，它由化合物X制备而成，化合物X是甲基甲基亚磺酰甲基硫醚锂盐与2 - (1 - 萘氧基) - 乙醛反应的产物。化合物X是三种非对映异构α - 羟基二硫代缩醛衍生物的混合物，用原甲酸乙酯处理时，得到所需的缩醛V以及两种闭环产物，二氢萘并[1,2 - b]吡喃VI和VII。根据质谱以及1H - 和13C - NMR数据对化合物VI和VII进行了表征。这些化合物的立体化学是根据其乙酸酯（XI和XII）的300 - MHz 1H - NMR光谱确定的。
