Boron trifluoride etherate → 1,1,3,3-Tetraethoxy-2-methylpropane

Participants

Reaction Conditions

Reaction Steps

A solution of one equivalent of diethoxymethyl acetate and one equivalent of a ethyl propenyl ether/ethanol mixture is stirred at ambient temperature for 30 min. followed by the addition of 1.3 equivalents of triethyl orthoformate. After cooling to 5° C. 1.5 ml. of boron trifluoride etherate is added and the resulting exotherm (5° to 37° C.) is controlled with an ice bath. After stirring at ambient temperature overnight the yellow reaction solution is diluted with ether and washed with water, saturated aqueous sodium bicarbonate and again with water. Drying (MgSO4) followed by solvent removal afforded a 92% yield of oil which is shown by glc to be ~80% pure product, δ(TMS, CDCl3) 4.44 (d, 2H, CH--O); 3.3-4.0 (complex, 8H, ethyl methylene), ~2.1 (m, 1H, CH3 --CH), 1.1 (t, 12H, ethyl methyls), and 1.0 (d, 3H, CH3 --CH).

Provenance & Evidence