Carbon Dioxide → HCID 67458593, compound

Participants

Reaction Conditions

Reaction Steps

To a dry flask was added 4-bromo-5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole (50 mg, 0.133 mmol) and THF (2669 μl), and the reaction mixture was cooled to −78° C. nBuLi (92 μl, 0.147 mmol) was added slowly and the reaction mixture was stirred at −78° C. for 30 min. Crushed dry ice was added, the reaction mixture was stirred at −78° C. for 20 min, quenched with 10% KHSO4, and allowed to warm to RT. The reaction mixture was extracted with EtOAc, dried over sodium sulfate and concentrated in vacuo to give 5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole-4-carboxylic acid (47 mg crude) to be used as is in the next step. MS: M+H=340.

Provenance & Evidence