Diethyl Ether → {2-[Dimethyl(thiophen-2-yl)silyl]phenyl}methanol

Participants

Reaction Steps

At 0° C., a solution of 2-thienylmagnesium bromide in THF (23 mL) [prepared from 2-bromothiophene (5.4 g, 33 mmol) and Mg (0.82 g, 34 mmol) was added to oxasilacyclopentane (7) (4.9 g, 30 mmol) in THF (10 mL) in accordance with Frisell, C.; Lawesson, S.-O. Org. Synth. Coll. Vol. 1972, 5, 642-644], and the resulting mixture was stirred at room temperature for 22 hours. The resulting mixture was diluted with diethylether and was filtered to remove unreacted magnesium. The filtrate was washed with a saturated NH4Cl aqueous solution, water, and brine, and then was dried over anhydrous MgSO4. After removal of the solvents under reduced pressure, the residue was purified by flash chromatography on silica gel, thereby obtaining (2-(hydroxymethyl)phenyl)dimethyl(2-thienyl)silane: 2d (5.9 g, yield of 79%) as a colorless oil, Rf: 0.21 (hexane-ethylacetate=5:1). 1H NMR (400 MHz, CDCl3) δ 7.64 (d, J=4.6 Hz, 1H), 7.57 (d, J=7.4 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.44 (t, J=7.4 Hz, 1H), 7.34-7.28 (m, 2H), 7.20 (dd, J=4.6, 3.4 Hz, 1H), 4.64 (s, 2H), 1.47 (s, 1H), 0.68 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 146.5, 138.5, 135.6, 135.3, 131.3, 130.2, 128.4, 128.2, 127.1, 65.3, 0.2; Anal. Calcd for C13H16OSSi; C, 62.85; H, 6.49. Found: C, 62.96; H, 6.49.

Provenance & Evidence