Chlorotrimethylsilane → HCID 15457428, compound

Temperature

-90 °C

A 1.3 M solution of s-BuLi in cyclohexane (40.7 mL, 52.9 mmol) was added to a liquid nitrogen-cooled solution of TMEDA (8.68 mL, 57.5 mmol) in THF (50 mL), maintaining the reaction temperature at -90° C. throughout the addition. The resulting solution was stirred 5 min, a solution of N-ethyl-4-fluoro-1-naphthalene-carboxamide (5.00 g, 23.0 mmol) in THF (15 mL) was added, and the resulting purple solution was stirred for 10 min at -90° C. TMSCl (8.76 mL, 69.0 mmol) was added, and after 10 min the cold bath was removed. The mixture slowly warmed to RT. The mixture was quenched with 100 mL 25% citric acid and extracted with ether (3×200 mL). The combined extracts were dried (MgSO4) and concentrated to a yellow powder which was purified by chromatography with ethyl acetate/hexanes to give 1.36 g of the desired amide, a 20% yield. m.p. 134-136° C.

1. additionthroughout the addition
2. stirringthe resulting purple solution was stirred for 10 min at -90° C
3. customafter 10 min the cold bath was removed
4. temperatureThe mixture slowly warmed to RT
5. customThe mixture was quenched with 100 mL 25% citric acid
6. extractionextracted with ether (3×200 mL)
7. dry with materialThe combined extracts were dried (MgSO4)
8. concentrationconcentrated to a yellow powder which
9. customwas purified by chromatography with ethyl acetate/hexanes

ORD record

ord-1cc8e50db3424b69902e50dc7bb7be66

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05994270