Hydrochloric Acid → HCID 14823629, compound

A solution of 1.5 grams (0.004 mole) of 5'-bromo-5-(4-methylphenyl) [2,2'-bithienyl] (prepared as in Example 64) in 25 ml of dry tetrahydrofuran was stirred, and 0.24 gram (0.0044 mole) of sodium methoxide in methanol was added. Upon completion of addition the reaction mixture was stirred at ambient temperature for three hours, then was heated under reflux for 16 hours. The reaction mixture was cooled and 50 ml of aqueous 10% hydrochloric acid was added. The mixture was extracted with methylene chloride and the extract dried with sodium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished with 25% methylene chloride in hexane. The appropriate fractions were combined and concentrated under reduced pressure to yield 0.6 gram of 5'-methoxy-5-(4-methylphenyl)[2,2'-bithienyl], m.p. 108°-111° C.

1. additionUpon completion of addition the reaction mixture
2. temperaturewas heated
3. temperatureunder reflux for 16 hours
4. temperatureThe reaction mixture was cooled
5. extractionThe mixture was extracted with methylene chloride
6. dry with materialthe extract dried with sodium sulfate
7. filtrationThe mixture was filtered
8. concentrationthe filtrate concentrated under reduced pressure to a residue
9. washElution
10. concentrationconcentrated under reduced pressure

ORD record

ord-8464fd9bb896459d89fac62f10f6a1fc

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04939165