1-Chloro-2,2-dimethylpropane → 2-(2,2-Dimethylpropyl)-n-ethyl-6-fluorobenzamide

Temperature

0 °C

A solution of p,p'-di-t-butyl biphenyl (5.559 g, 0.021 mol) and THF (100 mL) was stirred at 0° C. under an atmosphere of argon. Lithium wire (0.021 mol, 0.15 g) was added in small pieces and the mixture was allowed to stir at 0° C. for 24 h. The mixture was cooled to -78° C. and neopentyl chloride (2.0 g, 0.01875 mol) was added dropwise. The mixture was stirred at -78° C. for 1 h, and the compound of Example g (3.17 g, 0.015 mol) was added all at once. The mixture was continuously stirred or 4 h and 50 mL sat aq NaHCO3 was added. This mixture as extracted with three 50 mL portions of ethyl acetate. The combined extracts were washed twice with water, dried (MgSO4), and concentrated. The crude concentrate was purified by HPLC eluting with 1:4 ethyl acetate/hexanes. The oxazoline was as a clear oil in 27% yield.

1. temperatureThe mixture was cooled to -78° C.
2. stirringThe mixture was stirred at -78° C. for 1 h
3. stirringThe mixture was continuously stirred or 4 h
4. additionwas added
5. extractionThis mixture as extracted with three 50 mL portions of ethyl acetate
6. washThe combined extracts were washed twice with water
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. concentrationThe crude concentrate
10. customwas purified by HPLC
11. washeluting with 1:4 ethyl acetate/hexanes

ORD record

ord-2a2024358ab94db0a3b7bcd2b19dd1c5

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06028101