Carbon Dioxide → HCID 18324166, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 240 mg (0.84 minol) of 2,2,4,4-tetramethyl-6-bromothiochroman in 1 ml of dry ether at -78° C. was added, dropwise under nitrogen, 1 ml of 1.7M (1.7 mmol) tert-butyl lithium in pentane. The reaction mixture was stirred at -78° C. for a further 2 h and then treated quickly with an excess of dry ice. The reaction mixture was warmed to room temperature and treated with 1 ml of water and 1 ml of ether. The aqueous layer was separated and the organic layer was extracted with 4×5 ml of water. The aqueous extracts were combined, acidified with HCl to a pH of 2 and then extracted with 2×15 ml of ether. The ether extracts were combined, washed with water and saturated NaCl solution and then dried (MgSO4). The ether solution was filtered and the solvent removed in-vacuo to give the title compound as a white solid. PMR (CDCl3): δ1.42 (6H, s), 1.43 (6H, s), 2.03 (2H, s), 7.50 (1H, d, J~8.4 Hz), 7.81 (1H, dd, J~8.4 Hz, 1.8 Hz), 7.89 (1H, d, J~1.8 Hz).

Provenance & Evidence