2-Ethylthiophene → 5-Bromo-2-methoxyphenyl-5-ethyl-2-thienylmethanol

Temperature

-78 °C

A solution of 2-ethylthiophene (3.00 g) in tetrahydrofuran (36 ml) was cooled to 0° C. under argon atmosphere, and thereto was added dropwise n-butyl lithium (1.56 M hexane solution, 17.1 ml). The mixture was stirred at the same temperature for 30 minutes, and cooled to −78° C., and thereto was added dropwise a suspension of 5-bromo-2-methoxybenzaldehyde (5.74 g) in tetrahydrofuran (60 ml). The mixture was stirred at the same temperature for 2 hours, warmed to 0° C., and thereto was added a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, and the extract was washed with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-85:15) to give 5-bromo-2-methoxyphenyl-5-ethyl-2-thienylmethanol (5.99 g) as a pale yellow syrup. APCI-Mass m/Z 309/311 (M+H−H2O).

1. additionwas added dropwise
2. stirringThe mixture was stirred at the same temperature for 2 hours
3. temperaturewarmed to 0° C.
4. extractionThe mixture was extracted with ethyl acetate
5. washthe extract was washed with brine
6. dry with materialdried over sodium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-85:15)

ORD record

ord-5cce99c3ca6f4d61994addaa8b0a75f4

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785403B2