Dimethyl Sulfate → 5-methyl-[2,2']bithiophene

Temperature

-5 °C

Under a nitrogen atmosphere a stirred solution of 32.0 grams (0.193 mole) of 2,2'-bithienyl in 150 mL of diethyl ether was cooled to -5°0 C., and 90.5 mL (0.226 mole--2.6M in hexanes) of n-butyllithium was added slowy dropwise. Upon completion of addition the reaction mixture was stirred at -5° C. for one hour, and then a solution of 27.8 grams (0.220 mole) of dimethylsulfate in 75 mL of diethyl ether was added very slowly dropwise. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred for 18 hours. After this time the reaction mixture was poured into 350 mL of an aqueous 10% ammonium chloride solution. The mixture was extracted with diethyl ether, and the combined extracts were washed with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was distilled under reduced pressure to yield 30.0 grams of 5-methyl(2,2'-bithienyl); b.p. 108°-113° C./1.9 mm.

1. additionUpon completion of addition the reaction mixture
2. additionUpon completion of addition the reaction mixture
3. temperatureto warm to ambient temperature where it
4. stirringstirred for 18 hours
5. extractionThe mixture was extracted with diethyl ether
6. washthe combined extracts were washed with water
7. dry with materialThe organic layer was dried with magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
10. distillationThe oil was distilled under reduced pressure

ORD record

ord-5e72322afbc040caabbbe5c645a16f8b

Source dataset

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04826829