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The synthesis of the title compounds was accomplished by (i) boron trifluoride etherate catalysed alkylation of digitoxigenin with diazoalkanes, (ii) silver tetrafluoroborate assisted solvolysis of 3-desoxy-3α-iododigitoxigen 2d in an alcoholic medium, and (iii) m-chloroperbenzoic acid induced oxidative solvolytic displacement on the iodo compound 2d in the presence of alcohols. The third process was the most useful for the preparation of the mono ethers 2e and 2f of ethylene glycol and glycerol, respectively.
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Greenhouse et al. (1981) studied this question.
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