Thioanisole → HCID 19000564, compound

Participants

Reaction Steps

To a solution of thioanisol (3.73 g, 30 mmol) in a mixture of dry THF (50mL) and HMPA (14 mL) is added dropwise a solution of tert-butyllithium in pentane (30 mmol) at -78° C. over a period of 10 minutes. The resulting yellow-orange mixture is stirred at ambient temperature for an additional 45 minutes. A solution of 1-formyl-cyclopent-1-ene (2.88 g, 30 mmol) in dry THF (10 mL) is then added slowly. After stirring for 5 minutes, the reaction mixture is quenched with saturated ammonium chloride (20 mL), and allowed to warm to room temperature. The mixture is diluted with H2O (100 mL) and extracted with ethyl acetate (50 mL×3). The combined extracts are washed with H2O, dried (Na2SO4) and evaporated in vacuo to dryness. The residue is chromatographed over a silica gel column (5×30 cm) using toluene/EtOAc (9:1) as the eluent. The desired product is obtained as a pale yellow syrup, 5.0 g (76%). 1H NMR (CDCl3): δ1.66-1.99 (2H, m, CH2 -4'), 2.16-2.38 (4H, m, CH2 -3' and CH2 -5'), 2.61 (1H, brs, OH), 2.98 (1H, dd, J=8.21 Hz, J=13.45 Hz, Ha-2), 3.23 (1H, dd, J=4.39 Hz, J=13.45 Hz, Hb-2), 4.33 (1H, dd, J=4.39, J=8.21 Hz, H-1), 5.67 (1H, brs, H-1'), 7.14-7.45 (5H, m, Ph). Anal. Calc'd for C13H16OS: C, 70.87; H, 7.32; S, 14.34. Found: C, 70.88; H, 7.83; S, 14.37.

Provenance & Evidence