Dimethylformamide → tert-Butyl-dimethyl-(1-methyl-1-propyl-prop-2-ynyloxy)-silane

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Reaction Steps

An oven dried flask was charged with 3-methyl-hex-1-yn-3-ol (1.02 g, 0.009 mol) and dry DMF (9.0 mL). To this solution, cooled in an ice bath, was added Et3N (4.6 mL, 0.033 mol) followed by dropwise addition of tert-butyldimethylsilyl trifluoromethanesulfonate (2.9 g, 0.016 mol) under nitrogen atmosphere. The resulting mixture was stirred at RT for 18 h and then diluted with EtOAc (50 mL). The organic layer was washed with a saturated solution of NH4Cl (30 mL), water (4×20 mL), brine (40 mL), dried over sodium sulfate, and evaporated to afford the desired compound (2.05 g, 99.6%), as a yellow oil, used in the next step without further purification. Rf 0.9 (EtOAc/hexanes 1/9); 1H NMR (CDCl3) δ 0.152 (s, 3H), 0.156 (s, 3H), 0.85-0.84 (m, 9H), 0.91 (t, J=6.69 Hz, 3H), 1.41 (s, 3H), 1.61-1.44 (m, 4H), 3.37 (s, 1H).

Provenance & Evidence