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

HRID 42743Notes

Reaction equation

N#N.[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[O:16][C:15]([C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=2)[N:7]=1)([O-:5])=[O:4].[CH2:20](O)[CH2:21][OH:22].COC(OC)OC.F[B-](F)(F)F.[Li+].C([O-])(O)=O.[Na+]>CC(=O)OCC>[CH3:18][C:17]1([C:15]2[O:16][C:12]([CH2:11][N:8]3[N:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:10]=[N:9]3)=[CH:13][CH:14]=2)[O:22][CH2:21][CH2:20][O:19]1

Participants

Conditions

Temperature: 95 °C

Procedure

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.

Workup

customIn a flame dried round-bottomed flask equipped with a magnetic stir bar
temperatureto cool to rt
extractionthe aq. phase was extracted with EA (2×10 mL)
washextracts were washed with brine (10 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (60:30 hept-EA)

Sources & evidence

ORD record: ord-e1f977cbf9dd49a397633ec8b466e67b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Reaction notes

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