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29.8.2.2.1.2 Variation 2: Cleavage To Give Monoprotected 1,4-Diols

DOI: 10.1055/sos-SD-029-00478

Kouklovsky, C.Science of Synthesis, (200729598.

The reduction of 2-phenyl-1,3-dioxepanes with hydride reagents gives monobenzyl ethers of 1,4-diols. Diisobutylaluminum hydride, alane (obtained from lithium aluminum hydride and aluminum trichloride), or borane are commonly used as the reducing reagent. Thus, butane-1,4-diol is transformed into 4-(benzyloxy)butan-1-ol (248) via formation of the 1,3-dioxepane 247 and subsequent reduction (Scheme 164);[‌338‌] the preparation of the 4-methoxybenzyl analogue has been also reported.[‌338‌]

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