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 for 4 h and 50 mL sat aq NaHCO3 was added. This mixture was 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 for 4 h
4. additionwas added
5. extractionThis mixture was 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-17c22ab98f7647d9931fbfa7dfa80e5d

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998466