Triethylamine → 3,3-Diethoxy-1-propene

Participants

Reaction Steps

A solution of diol (Molecule 2.1) (1.5 g, 7.8 mmol) in 7.5 ml of dry DMF was treated with acrolein dimethyl acetal (4.62 ml, 39 mmol) and PTSA.H2O (0.371 g, 1.95 mmol). After stirring for 24 h at room temperature the reaction was stopped by addition of 1 ml of Et3N and poured out in 200 ml of H2O. The aqueous phase was extracted with toluene (3×100 ml) and the combined organics were washed once with brine (100 ml) and dried over MgSO4. Column chromatography of the residue over silica gel (cyclohexane/ethyl acetate: 85/15) afforded Molecule 2.2 (FIG. 4) as white crystals (1.306 g, 5.67 mmol, 73%).

Provenance & Evidence