Isobutylene → HCID 21566090, compound

Participants

Reaction Steps

4.7 g. of 1,1-ethylenedioxy-2-(6-tert.-butoxycarbonylhexyl)-3-(2-hydroxy-2-methylheptylthio)-cyclopentane (obtainable from 2-(6-carboxyhexyl)-2-cyclopentenone, addition of 2-hydroxyheptanethiol, subsequent ketalization with ethylene glycol, as well as oxidation with CrO3 in ether, addition to isobutylene, and reaction of the thus-obtained 1,1-ethylenedioxy-2-(6-tert.-butoxycarbonylhexyl)-3-(2-oxoheptylthio)-cyclopentane with methylmagnesium bromide) is agitated for 2 hours at room temperature in 60 ml. of 2N aqueous HCl, extracted, after cooling, three times with CH2Cl2 ; the organic phase is washed with water, dried over Na2SO4, the solvent is distilled off, and chromatographic purification of the residue (silica gel/chloroform) yields 2-(6-carboxyhexyl)-3-(2-hydroxy-2-methylheptylthio)-cyclopentanone. Rf = 0.25 (silica gel/chloroform : methanol = 95 : 5).

Provenance & Evidence