Tetrahydrofuran → HCID 117787369, compound

Temperature

-78 °C

To a solution of 2-bromo-1,3,5-trimethylbenzene (1.22 g) in tetrahydrofuran (20.0 mL) was added a 1.59 M solution of n-butyllithium in n-hexane (3.86 mL) at −78° C., followed by stirring at −78° C. for 30 minutes. Subsequently, a solution of tert-butyl (4-bromo-2-thienyl)acetate (1.55 g) in tetrahydrofuran (15.0 mL) was added thereto, followed by stirring at −78° C. for 30 minutes. Subsequently, a 1.59 M solution of n-butyllithium in n-hexane (3.51 mL) was added thereto at −78° C., followed by stirring at −78° C. for 30 minutes. Further, N,N-dimethylformamide (0.451 mL) was added thereto, followed by stirring at −78° C. for 1 hour. To the reaction mixture were added a saturated aqueous ammonium chloride solution and ethyl acetate, and the organic layer was extracted. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl (4-formyl-2-thienyl)acetate (355 mg).

1. stirringby stirring at −78° C. for 30 minutes
2. customat −78° C.
3. stirringby stirring at −78° C. for 30 minutes
4. stirringby stirring at −78° C. for 1 hour
5. extractionthe organic layer was extracted
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

ORD record

ord-73900e6f5a2841d79b4613bd8a02f8c4

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199927B2