Dimethylformamide → Silane, [(3,6-dihydro-2H-pyran-4-yl)oxy]trimethyl-

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Reaction Conditions

Reaction Steps

To a flame-dried sealed tube was added DMF (3 ml) and triethylamine (3.34 ml, 23.97 mmol), followed by tetrahydro-4H-pyran-4-one (0.923 ml, 9.99 mmol) and TMS-Cl (1.532 ml, 11.99 mmol). The mixture was heated at 140° C. for 16 hours, allowed to cool to room temperature, diluted with pentane and decanted into ice cooled saturated sodium bicarbonate and extracted with pentane (50 ml×3). The combined pentane layers were washed with brine and dried over sodium sulfate, filtered and concentrated to give 1.0 g of the product as a liquid (5.80 mmol, yield 58.1%). 1H NMR (400 MHz, CDCl3) δ (ppm) 4.63-4.61 (m, 1H), 3.95-3.93 (m, 2H), 3.60-3.58 (m, 2H), 1.94-1.90 (m, 2H), 0.01 (b, 9H).

Provenance & Evidence