Tetrahydrofuran → HCID 67001330, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (1.5 mmol in 60% mineral oil) in THF (6 mL) at 0° C. was added triisopropylsilyl thiol (1.5 mmol) and the solution was stirred for 1 h before 3-(4-bromo-phenyl)-5-(3-chloro-benzyl)-4-methoxymethyl-4H-[1,2,4]triazole (1.5 mmol) in benzene (6 mL), triphenyl phosphine (0.6 mmol), and Pd2(dba)3 (0.08 mmol) were added. After bubbled argon through the solution for 15 min, the mixture was stirred at 80° C. for 18 h before it was cooled to room temperature. The reaction mixture was diluted with water (30 mL) and the resulting mixture was extracted with a solution of toluene and ethyl acetate (4:1) and the organic phase was washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography to give 3-(3-chloro-benzyl)-4-methoxymethyl-5-(4-triisopropylsilanylsulfanyl-phenyl)-4H-[1,2,4]triazole and 3-(3-chloro-benzyl)-1-methoxymethyl-5-(4-triisopropylsilanylsulfanyl-phenyl)-1H-[1,2,4]triazole (1.0 mmol) as a mixture of two isomers (4:1).

Provenance & Evidence