Methanol → HCID 70094791, compound

Participants

Reaction Steps

To a solution of sodium hydride (108 mg of a 60% dispersion in mineral oil, 2.7 mmol) and ethyl formate (0.55 mL, 6.8 mmol) at 0C in THF (5 mL) was added a solution of 6,6-dimethyl-3-methylthio-1-(pyrid-2-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (205 mg, 0.68 mmol) in THF (5 mL). The mixture was stirred at room temperature for 2 h then more sodium hydride (50 mg of a 60% dispersion in mineral oil, 1.3 mmol) and ethyl formate (0.55 mL, 6.8 mmol) were added. The mixture was stirred for a further 2 h before MeOH (0.2 mL) was added and the mixture evaporated in vacuo. The residue was dissolved in water (20 mL) and the undissolved solid filtered off. The mixture was acidified to pH 1 using 1M HCl then neutralised with Na2CO3. The mixture was partitioned between EtOAc (20 mL) and water (10 mL) and the organic layer separated and dried (MgSO4). The solvent was evaporated and the residue triturated with ether to afford the title compound (90 mg, 40%) as a yellow solid. 1H NMR (250 MHz, CDCl3) δ1.21 (6H, s), 2.70 (3H, s), 2.93 (2H, s), 7.16-7.22 (1H, m), 7.4.3 (1H, d, J=8.0 Hz), 7.57 (1H, d, J=10.4 Hz), 7.74 (1H, d of t, J=7.7 and 1.8 Hz), 8.62-8.65 (1H, m), 14.68 (1H, d, J=10.4 Hz). MS (ES+) 332 (M+1).

Provenance & Evidence