반응 #71027

반응 방정식

N2

4-nitro-2H-[1,2,3]triazole

DIPEA

2-(5-chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane

→

title compound

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

용매

EA

Water

DMF

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   추출The aq. layer was extracted with EA (100 mL)
3. 3
   건조extracts were dried over MgSO4
4. 4
   여과filtered
5. 5
   기타the solvents were removed under reduced pressure
6. 6
   기타Purification of the residue by FC (2:1 hept-EA)

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-nitro-2H-[1,2,3]triazole (875 mg, 7.67 mmol) in DMF (7.0 mL) was treated at rt with DIPEA (2.63 mL, 15.34 mmol). After 30 min, a solution of 2-(5-chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane (1.87 g, 9.21 mmol) in DMF (7.0 mL) was added and the reaction mixture was stirred for 16 h at 50° C. Water (100 mL), followed by EA (100 mL) were added. The aq. layer was extracted with EA (100 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as an orange oil: TLC:rf (2:1 hept-EA)=0.26. LC-MS-conditions 02: tR=0.95 min; [M+H]+=281.01.

출처