Solketal → 2,2-Dimethyl-1,3-dioxolane-4-methanol 3,5-bistrifluoromethylbenzyl ether

Beteiligte Stoffe

Reaktionsschritte

To a stirred solution of solketal (0.151 mol) in DMF/THF (1:1, 300 ml) under a nitrogen atmosphere was added sodium hydride (1.2 equivalents of an 80% dispersion in mineral oil). The anion was allowed to form over one hour prior to addition of 3,5-bistrifluoromethylbenzyl bromide. The reaction was partitioned between ethyl acetate-saturated ammonium chloride after 1 h and the organic phase separated, dried (MgSO4), and concentrated to a yellow oil. Chromatography using pet. ether then 20% ethyl acetate-pet. ether as eluent gave 2,2-dimethyl- 1,3-dioxolane-4-methanol-3,5-bistrifluoromethylbenzyl ether as a yellow oil: (CDCl3) δ1.4 (3H, s), 1.45 (3H, s), 3.6-3.65 (2H, m), 3.7-3.8 (1H, m), 4.1-4.15 (1H, m), 4.3-4.4 (1H, m), 4.7 (2H, s), 7.8 (3H, s).

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