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High yield protection of alcohols, including tertiary and base sensitive alcohols, as benzhydryl ethers by heating with diphenyldiazomethane in the absence of any other reagent |
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| Authors: | Daniel Best Sebastian D. Rule Thomas B. Mercer Alexander C. Weymouth-Wilson Sigthor Petursson |
| Affiliation: | a Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK b Faculty of Business and Science, University of Akureyri, IS-600 Akureyri, Iceland c Dextra Laboratories Limited, The Science and Technology Centre, Whiteknights Road, Reading RG6 6BZ, UK |
| Abstract: | A protecting group that can be introduced efficiently without the need for any acid or base catalysis and which is not prone to acid or base catalysed migration is a significant advantage for many syntheses. Benzhydryl [diphenylmethyl] ethers of sugar lactones are formed in high yield under neutral conditions when the corresponding alcohol is heated with diphenyldiazomethane in an inert solvent such as acetonitrile or toluene; this allows the easy protection of base sensitive and highly hindered tertiary alcohols in the absence of any other reagents. |
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