Diethyl Ether → 1,3-Dioxolane-2-propanal, 2-methyl-

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Reaction Steps

To a solution of 2-2 (44.74 g, 0.22 mol) in 400 mL THF at -78° C. was added DIBAL (264 mL 1 M in hexanes, 0.264 mol) over 10 minutes. After stirring for 1 h, 350 ml of 1.0 M Rochelle's salt and 300 ml ether were added followed by the removal of the cooling bath. After stirring for 1 h, the organic portion was separated and dried over Na2SO4. Evaporative removal of the solvent gave 2-3 as a colorless oil. TLC Rf =0.80 (silica, ethyl acetate). 1H NMR (300 MHz, CDCl3) δ 9.73 (s, 1H), 3.50 (d, 1H, J=16 Hz), 2.61 (d, 1H, J=21 Hz), 2.48 (m, 1H), 2.07 (t, 1H, J=7H), 1.33 (s, 3H).

Provenance & Evidence