Triisopropylsilyl chloride → HCID 90303362, compound

Temperature

-78 °C

At −78° C., a soln. of n-BuLi in hexanes (2.18 M, 16.7 mL, 36.4 mmol) was added over 30 min to a soln. of 5-bromo-4-(oxiran-2-ylmethoxy)thiazole (7.17 g, 30.4 mmol) in THF (564 mL). The mixture was stirred at −78° C. for 2 h, then, TIPSCl (6.63 mL, 31.0 mmol) was added, the mixture was allowed to warm to RT and stirred at RT for 30 min. Subsequently, the mixture was cooled to −78° C. and treated with a soln. of n-BuLi in hexanes (2.18 M, 13.9 mL, 30.4 mmol). The mixture was stirred at 0° C. for 2 h, then, it was quenched with aq. sat. NaHCO3 and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. The residue was purified by means of CC (100 g KP-Sil, EtOAc/Hept 5-50%), followed by CC (5-50% EtOAc/Hept) to provide a yellow oil.

1. customAt −78° C.
2. temperatureto warm to RT
3. stirringstirred at RT for 30 min
4. temperatureSubsequently, the mixture was cooled to −78° C.
5. additiontreated with a soln
6. stirringThe mixture was stirred at 0° C. for 2 h
7. customit was quenched with aq. sat. NaHCO3
8. extractionextracted with EtOAc
9. washlayers were washed with brine
10. dry with materialdried over MgSO4
11. customThe residue was purified by means of CC (100 g KP-Sil, EtOAc/Hept 5-50%)
12. customto provide a yellow oil

ORD record

ord-1d9ff18294014e0c9c9513130e919f74

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388197B2