تفاعل #58002

معادلة التفاعل

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

المذيبات

ethanol toluene

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted three times with EtOAc
2. 2
   غسيلThe combined organic extracts were washed with brine
3. 3
   تجفيفdried (MgSO4)
4. 4
   ترشيحfiltered
5. 5
   تركيزthe filtrate concentrated in vacuo
6. 6
   أخرىPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-25% EtOAc/hexanes as eluent)

الإجراء التجريبي

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.

المصدر