Hydrochloric Acid → (3-Methylthiophen-2-yl)(4-propylphenyl)methanone

Temperatur

-78 °C

To a solution of 4-bromophenetole (1.86 mL, 13.0 mmol) in anhydrous THF (15 mL) was added dropwise (over a 5-min period) a solution of n-BuLi (6.0 mL, 2.5 M in hexane) under nitrogen atmosphere at −78° C. The resulting mixture was stirred at −78° C. for 1 hour, and then a solution of the Weinreb amide 43 (1.85 g, 10.0 mmol) in anhydrous THF (5.0 mL) was added dropwise (over a 10-min period). The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. The mixture was poured into a 1 M HCl solution (25 mL) and extracted with EtOAc (50 mL). The organic phase was subsequently washed with brine, dried over MgSO4 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide (4-ethoxyphenyl)(3-methylthiophen-2-yl)methanone (44, 1.52 g, 6.16 mmol, 62%).

1. temperatureto warm to room temperature
2. stirringstirred for 16 hours
3. extractionextracted with EtOAc (50 mL)
4. washThe organic phase was subsequently washed with brine
5. dry with materialdried over MgSO4
6. customevaporated under vacuum
7. customThe residue was further purified by silica column chromatography (Biotage)

ORD-Eintrag

ord-3ba859f9ba104090af2929a15cbc8a55

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09006187B2