Tetrahydrofuran → HCID 11989419, compound

Participants

Reaction Steps

At 0° C., a 0.5 M THF solution of 2-methyl-1-propenylmagnesium bromide (100 mL, 50 mmol) was added to a solution of oxasilacyclopentane (7) (7.5 g, 46 mmol) in THF (50 mL), and the resulting mixture was stirred at room temperature overnight and then was diluted with diethyl ether. The resulting mixture was washed with a saturated NH4Cl aqueous solution, water, and brine, and then was dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was purified by flash chromatography on neutral aluminum oxide (activity grade III), thereby obtaining (2-(hydroxymethyl)phenyl)dimethyl(2-methyl-1-propenyl)silane: 1g (7.1 g, yield of 71%) as a colorless oil, Rf: 0.26 (hexane-ethyl acetate=5:1). 1H NMR (400 MHz, C6D6) δ 7.57 (d, J=7.3 Hz, 1H), 7.45 (d, J=7.7 Hz, 1H), 7.22 (dd, J=7.4, 7.3 Hz, 1H), 7.13 (dd, J=7.7, 7.4 Hz, 1H), 5.41 (s, 1H), 4.63 (d, J=5.9 Hz, 2H), 1.78 (t, J=5.9 Hz, 1H), 1.66 (s, 3H), 1.46 (s, 3H), 0.37 (s, 6H); 13C NMR (101 MHz, C6D6) δ 153.4, 147.3, 137.5, 134.9, 129.7, 128.0, 127.0, 123.8, 65.3, 29.3, 23.2, 0.0; Anal. Calcd for C13H20Osi; C, 70.85; H, 9.15. Found: C, 70.83; H, 9.23.

Provenance & Evidence