Sodium Bicarbonate → HCID 68743336, compound

Participants

Reaction Steps

Methyl triphenylphosphonium iodide (1.56 g, 3.87 mmol) was dissolved in 25 mL ether in a 50 ml round-bottom flask at 0° C. under dry nitrogen. To the mixture was added in one portion potassium tert-butoxide (0.46 g, 4.15 mmol) and was stirred for 10 min at room temperature. 2-(3-naphtylsulfanyl)benzenecarbaldehyde (0.73 g, 2.77 mmol) was added in one portion at 0° C. and the reaction mixture was stirred for additional 2.5 h at room temperature. The mixture was added to 50 mL, of saturated sodium bicarbonate solution, and extracted with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The light yellow oil of the crude product was further purified by chromatography on silica gel using 9:1 petroleum ether 60-80: ether as eluent to afford a colorless oil (0.58 g, 81%). 1H-NMR (500 MHz, CDCl3): δ 5.35 (dd, J=1.3, 11.0 Hz, 1H), 5.77 (dd, J=1.3, 17.5 Hz, 1H), 7.24-7.51 (m, 7H), 7.67-7.81 (m, 5H) ppm. 13C-NMR (125 MHz, CDCl3): δ 116.28, 125.85, 126.20, 126.50, 127.22, 127.48, 127.68, 127.97, 128.24, 128.49, 128.70, 131.91, 132.81, 133.72, 133.78, 133.81, 134.52, 139.71 ppm. E1-MS: m/z M+ Calc. 262.3, found 262.2.

Provenance & Evidence