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

Temperature

-50 °C

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).

1. additionare introduced into a 3-necked round-bottomed flask under nitrogen
2. temperaturecooled to −78° C
3. customto return to room temperature
4. extractionThe water-THF mixture is extracted three times with 300 mL of Et2O
5. washThe resulting organic phase is washed several times with saturated aqueous NaCl solution
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe solid collected
9. customis recrystallised from methanol

ORD record

ord-68309f7c260c41579dfd45caa435444c

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07416682B2