Imidazole → Ethyl (S)-(-)-2-(tert-butyldimethylsilyloxy)propionate

Participants

Reaction Steps

To a solution of (S)-(−)-ethyl lactate (37.4 g, 0.32 mol) in DCM (200 mL) was added imidazole (25.75 g, 0.38 mol) and TBSCl (50 g, 0.33 mol). The reaction mixture was stirred at room temperature for 2 hours. The reaction was diluted with water and extracted with DCM (2×50 mL), the combined organic extracts washed with brine dried (MgSO4) and concentrated in vacuo to give the title product as a colourless oil (100%). 1H NMR (CDCl3, 400 MHz) 4.21 (1 H, q, J=6.73 Hz), 4.14-4.01 (2H, m), 1.29 (3H, d, J=6.79 Hz), 1.18 (3H, t, J=7.09 Hz), 0.80 (9H, s), −0.01 (6H, s).

Provenance & Evidence