Chlorotrimethylsilane → HCID 10013095, compound

Participants

Reaction Steps

A suspension of zinc dust (39.2 g, 0.6 mol) in 150 ml of THF and 150 ml of B(OCH3)3 is activated with 1,2 dibromoethane (3.0 ml) and chlorotrimethylsilane (3.0 ml). Diethyl ketone (95.7 ml, 0.9 mol) is added to the activated zinc suspension. Ethyl 2-bromo-2-methylpropanoate (Fuka, Buchs, Schweiz) is added dropwise within 90 min to the mixture. The mixture is stirred at r.t. for 20 h. The reaction is quenched by addition of concentrated aqueous ammonia solution (150 ml) at 0° C. Glycerine (150 ml) and diethyl ether (150 ml) is added and the organic layer is separated. The aqueous layer is extracted twice with diethyl ether. The combined organic layers are dried over magnesium sulfate and concentrated in vacuo. Purfication of the residue by vacuum distillation affords ethyl 2,2-dimethyl-3-ethyl-3-hydroxypentanoate 22 (56.65 g, 47%) as a colourless liquid (b.p. 108-110° C./10 mbar). 13C-NMR (100 MHz, CDCl3): δ=179.2; 76.2; 60.9; 50.3; 28.2; 21.6; 14.1; 8.9

Provenance & Evidence