Dimethylformamide → HCID 86675605, 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 (810 mg, 2.162 mmol) and THF (21.6 mL), and the reaction mixture was cooled to 78° C. nBuLi (1.486 mL, 2.378 mmol) was added slowly and the reaction mixture was stirred at −78° C. for 5 min. DMF (0.837 mL, 10.81 mmol) was added and the reaction mixture was stirred at −78° C. for 10 min, quenched with water, allowed to warm to RT. The reaction mixture was extracted with EtOAc, washed with 3M LiCl, dried over sodium sulfate and concentrated in vacuo to give 5-[(4-chlorophenyl)sulfanyl]-2-(tetrahydro-2H-pyran-4-yl)-1,3-oxazole-4-carbaldehyde (830 mg crude) to be used as is in the next step. MS: M+H=324.

Provenance & Evidence