FIELD: chemistry.
SUBSTANCE: invention relates to methods of producing (1E)-1-tri-n-butylstannyl-4-methyl-4-trimethylsiloxyoct-1-ene of formula I , which is used in synthesis the vital analogue of misoprostol prostaglandin E1. Disclosed is a method which includes reacting, in an argon atmosphere, 4-methyl-4-trimethylsilyloxy-1-octane with tributyltin hydride while stirring and boiling for 3 hours, followed by separating the end product by vacuum distillation; wherein the tributyltin hydride used is formed in situ by adding sodium borohydride to tributyltin chloride in anhydrous ethanol while stirring in an argon atmosphere at 20°C.
EFFECT: method simplifies, lowers the cost and improves technological effectiveness of the production process by replacing the toxic and expensive tributyltin hydride with a reagent produced in situ from readily available and considerably cheaper sodium borohydride and tributyltin chloride, which enables to scale synthesis to hundreds of grams.
1 ex
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Authors
Dates
2015-08-20—Published
2014-07-29—Filed