Iodoethane → HCID 10442110, compound

Temperature

0 °C

A solution of diisopropylamine (17.1 g, 169 mmol) in THF (180 mL) was stirred under nitrogen at 0° C. n-Butyl lithium (n-BuLi-67.6 mL, 2.5 M in hexane) was added dropwise over 15 min and the resulting solution stirred for 0.5 h at 0° C. After this time period, the reaction was cooled to −78° C., and 4,4,4-trifluorobutyric acid (10.0 g, 70.4 mmol) in THF (20 mL) was added dropwise over 0.5 h. The resulting solution was stirred for an additional 0.5 h at −78° C. After this time period, ethyl iodide (6.19 mL, 77.4 mmol) was added dropwise over 15 min. The resulting solution was stirred for 15 min. at −78° C. then warmed to 25° C. for 24 h. After this time period, the reaction mixture was quenched by slow addition of H2O (˜20 mL). After concentration, the residue was acidified to pH 1 with 2 N aq. HCl and then extracted with Et2O (400 mL). The organic layer was then dried using MgSO4. After concentration, the resulting residue was used directly in the next reaction without further purification.

1. additionwas added dropwise over 15 min
2. temperatureAfter this time period, the reaction was cooled to −78° C.
3. stirringThe resulting solution was stirred for an additional 0.5 h at −78° C
4. stirringThe resulting solution was stirred for 15 min. at −78° C.
5. temperaturethen warmed to 25° C. for 24 h
6. customAfter this time period, the reaction mixture was quenched by slow addition of H2O (˜20 mL)
7. concentrationAfter concentration
8. extractionextracted with Et2O (400 mL)
9. customThe organic layer was then dried
10. concentrationAfter concentration
11. customthe resulting residue was used directly in the next reaction without further purification

ORD record

ord-ef98e3eaddda45d5a7c912ae1ac73502

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07300951B2