반응 #1606359

반응 방정식

2,2,6,6-tetramethylpiperidine

n-butyllithium

tert-butyl(2-cyclohexyl-6-fluorophenoxy)dimethylsilane

triisopropyl borate

→

title compound

수율 101.5%

(3-((tert-Butyldimethylsilyl)oxy)-4-cyclohexyl-2-fluorophenyl)boronic acid

수율 101.5%

용매

THF

반응 조건

후처리

1. 1
   온도the reaction was warmed to rt for 5 minutes
2. 2
   온도before cooling back down to −78° C
3. 3
   workup.STIRRINGstirred for 5 minutes
4. 4
   온도The reaction mixture was warmed to rt
5. 5
   기타quenched with saturated NH4Cl (2 mL)
6. 6
   추출extracted with EtOAc (2×5 mL)
7. 7
   세척The combined organic extracts were washed with brine (3×5 mL)
8. 8
   건조dried over MgSO4
9. 9
   여과filtered
10. 10
    농축concentrated to dryness

실험 절차

A solution consisting of 2,2,6,6-tetramethylpiperidine (0.50 mL, 3.0 mmol) and dry THF (2 mL) was cooled to −78° C. and treated with n-butyllithium (1.1 mL, 2.75 mmol, 2.5 M in hexanes). After stirring for 5 minutes, the reaction was warmed to rt for 5 minutes before cooling back down to −78° C. The reaction was then treated with tert-butyl(2-cyclohexyl-6-fluorophenoxy)dimethylsilane (0.719 g, 2.33 mmol) and triisopropyl borate (0.60 mL, 2.6 mmol) and stirred for 5 minutes. The reaction mixture was warmed to rt, quenched with saturated NH4Cl (2 mL), and extracted with EtOAc (2×5 mL). The combined organic extracts were washed with brine (3×5 mL), dried over MgSO4, filtered, and concentrated to dryness to yield the title compound (0.833 g, 101%), which was used without purification.

출처