Water → 6-Methoxy-2-methylbenzo[b]thiophene

Participants

Reaction Conditions

Reaction Steps

20.20 g (0.12 mol) of 6-Methoxybenzo[b]thiophene diluted in 450 mL of anhydrous THF are introduced into a 3-necked round-bottomed flask under nitrogen. The mixture is cooled to −50° C. 64 mL (0.14 mol) of a 2.5M solution of nBuLi in hexane are added dropwise. The resulting mixture is stirred for 1 h30 at −40° C. and then cooled to −78° C. 52 g (0.36 mol) of MeI are added. The mixture is allowed to return to room temperature, then hydrolysed with 250 mL of water. The water-THF mixture is extracted three times with 300 mL of Et2O. The resulting organic phase is washed several times with saturated aqueous NaCl solution, dried over magnesium sulfate and then concentrated under reduced pressure. The solid collected is recrystallised from methanol to give a white solid (21.25 g, 97% yield).

Provenance & Evidence