2,2-Dimethyl-5-[3-(diphenylstannyl) propyl]-1,3-dioxolan-4-one

Abstract

[410098-22-5] C20H24O3Sn (MW 431.10) InChI = 1S/C8H13O3.2C6H5.Sn.H/c1-4-5-6-7(9)11-8(2,3)10-6;2*1-2-4-6-5-3-1;;/h6H,1,4-5H2,2-3H3;2*1-5H;; InChIKey = PUVIBBRSMWZAIC-UHFFFAOYSA-N (title reagent behaves similar to Bu3SnH and Ph3SnH in standard free radical reactions,1 but the tin-containing by-products can be removed easily from the desired reaction products by mild hydrolysis under basic or acidic conditions1) Physical Data: colorless oil. Solubility: soluble in common organic solvents; usually used in benzene or toluene. Preparative Methods: 2-hydroxy-4-pentenoic acid,2 prepared from glyoxylic acid hydrate, is ketalized using 2,2-dimethoxypropane and TsOH·pyridine; the ketal is hydrostannylated by heating with an excess of triphenyltin hydride, and treatment of the resulting stannane with 1 equiv of I2,3 followed by reduction with sodium borohydride, gives the title compound. Purification: rapid flash chromatography over silica gel, using 1:4 ethyl acetate–hexane, affords the stannane as a colorless oil.1 Handling, Storage, and Precautions: the compound can be stored1 for several months in a freezer (−10 °C) in a sealed flask flushed with nitrogen, without significant decomposition, and is easily repurified, if necessary, by flash chromatography. The toxicity of this compound has not been studied and, as a precaution, work with this compound should be done in a fume hood and skin contact should be avoided.