반응 #71021

반응 방정식

NaHCO3

N2

1-[5-(4-nitro-[1,2,3]triazol-2-ylmethyl)-furan-2-yl]-ethanone

ethylene glycol

trimethylorthoformate

lithium tetrafluoroborate

→

title compound

2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-ylmethyl]-4-nitro-2H-[1,2,3]triazole

용매

EA

반응 조건

후처리

1. 1
   기타In a flame dried round-bottomed flask equipped with a magnetic stir bar
2. 2
   온도to cool to rt
3. 3
   추출the aq. phase was extracted with EA (2×10 mL)
4. 4
   세척extracts were washed with brine (10 mL)
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   기타the solvents were removed under reduced pressure
8. 8
   기타Purification of the residue by FC (60:30 hept-EA)

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark under inert atmosphere (N2), a solution of 1-[5-(4-nitro-[1,2,3]triazol-2-ylmethyl)-furan-2-yl]-ethanone (180 mg, 0.76 mmol) in ethylene glycol (0.85 mL, 15.24 mmol) was treated with trimethylorthoformate (0.17 mL, 1.52 mmol) and lithium tetrafluoroborate (14 mg, 0.15 mmol). The resulting mixture was heated to 95° C. overnight. The reaction mixture was allowed to cool to rt. NaHCO3 (10 mL) and EA (10 mL) were added and the aq. phase was extracted with EA (2×10 mL). The combined org. extracts were washed with brine (10 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (60:30 hept-EA) gave the title compound as a colorless oil: TLC:rf (60:30 hept-EA)=0.31. LC-MS-conditions 02: tR=0.94 min; [M+H]+=281.01.

출처