Methyl Chloroformate functional group protection

Functional Group Protection. The protection of alcohols and phenols as their methyl carbonates can be achieved using methyl chloroformate under basic conditions (eq 1). Primary and secondary alkylamines are readily protected as their methyl carbamates using MCF, typically in the presence of EtsN, - Na2C03, K2CO3, or NaHC03. Selective Af-protection of amino alcohols can be achieved under these conditions (eq 2). ... 

The furanone 42, although commercially available, could also be obtained in large amounts by epoxidation of 3,3-dimethyl-4-pentenoic acid with 3-chloroperoxybenzoic acid (MCPBA) in chloroform at room temperature (84%). After protection of the primary alcohol 42 as a benzyl ether, the carbonyl unit was reduced with diisobutylaluminum hydride in ether at -78 °C to afford the diastereomeric pair of lactols 43 in 97% yield and a ratio of approximately 2 1. The lactols were methylated with p-toluene sulfonic acid in methanol to provide the functionalized tetrahydrofurans in nearly quantitative yield. The benzyl group was removed by hydrogenolysis over palladium hydroxide on carbon to afford the alcohols 44 in 94% isolated yield use of other catalysts, such as palladium on carbon, gave less reproducible results. 

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