Hydrochloric Acid → HCID 66616139, compound

Participants

Reaction Steps

Sodium tert-butoxide (3.681 g, 38.3 mmol, 2.0 eq.) is suspended in anhydrous DMSO under nitrogen. To this a solution of methyl 4-vinylbenzoate (3.11 g 19.15 mmol, 1.0 eq.) and tosylmethyl isocyanide (4.86 g, 24.89 mmol, 1.3 eq.) in anhydrous DMSO is transferred via cannula. The dark brown mixture is stirred at room temperature for 16 hrs. The mixture is adjusted to pH 6 by addition of 10% HCl solution, diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic extract is washed with water (2×50 mL) and brine, dried over sodium sulfate and concentrated. The crude residue is purified by silica gel chromatography (20-40% ethyl acetate/hexanes) to give 990 mg (4.92 mmol, 25.7%) of methyl 4-(1H-pyrrol-3-yl)-benzoate as a cream colored solid. MS (ES+): m/e 201.08. 1H NMR (300 MHz, CDCl3): δ 8.39 (1H, br s), 8.00 (2H, d, J−9 Hz), 7.58 (2H, d, J=9 Hz), 7.20 (1H, m), 6.85 (1H, m), 6.60 (1H, m), 3.91 (3H, s).

Provenance & Evidence