반응 #58002

반응 방정식

triflate

4,5-dimethyl-2-propionylphenyl trifluoromethanesulfonate

sodium carbonate

tert-butyl 4(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)carboxylate

→

84

tert-butyl 4-(4,5-dimethyl-2-propionylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate

용매

ethanol toluene

반응 조건

후처리

1. 1
   추출extracted three times with EtOAc
2. 2
   세척The combined organic extracts were washed with brine
3. 3
   건조dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축the filtrate concentrated in vacuo
6. 6
   기타Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-25% EtOAc/hexanes as eluent)

실험 절차

A vigorously stirred solution of triflate 83 (10.5 g, 33.8 mmol), aqueous sodium carbonate (50.8 mL of a 2.0 M solution, 102 mmol), tert-butyl 4(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)carboxylate (10.45 g, 33.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (3.91 g, 3.38 mmol) in ethanol/toluene (1:1, 100 mL) was degassed via three vacuum/nitrogen ingress cycles and heated to 75° C. for 30 min. The reaction mixture was poured into ice water and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and the filtrate concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-25% EtOAc/hexanes as eluent) afforded 84 as a colorless oil.

출처