Potassium Carbonate → Tert-butyl-(2,2-dimethyl-but-3-ynyloxy)-dimethyl-silane

Participants

Reaction Steps

To a solution of 3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-propionaldehyde (0.84 g, 3.9 mmol) in methanol (20 mL) was added (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (0.9 g, 4.7 mmol) and K2CO3 (1.1 g, 7.8 mmol). The solution was stirred overnight at room temperature and then the reaction mixture was washed with water. The crude residue was purified by flash chromatography (eluted with: petroleum ether:EtOAc=100:2) to afford the title compound (0.17 g, 21%): 1H NMR (CDCl3, 400 MHz) delta 0.05 (s, 6H), 0.90 (s, 9H), 1.19 (s, 6H), 2.06 (s, 1H), 3.45 (s, 2H).

Provenance & Evidence