Hydrochloric Acid → 1-[5-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-furan-2-yl]-ethanol

HRID 42741Notes

Reaction equation

N#N.[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[O:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=2)[N:7]=1)([O-:5])=[O:4].[CH3:19][Al](C)C.[NH4+].[Cl-].Cl>C(Cl)Cl.CCCCCCC>[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[O:16][C:15]([CH:17]([OH:18])[CH3:19])=[CH:14][CH:13]=2)[N:7]=1)([O-:5])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(4-nitro-[1,2,3]triazol-2-ylmethyl)-furan-2-carbaldehyde (180 mg, 0.81 mmol) in CH2Cl2 (8.0 mL) was treated at −10° C. with trimethylaluminum (0.32 mL of a 2M solution in heptane, 0.64 mmol). The reaction mixture was stirred at 0° C. for 2 h then poured on sat. aq. NH4Cl (5 mL), diluted with CH2Cl2 (10.0 mL) followed by 1N HCl (10 mL). The mixture was extracted with CH2Cl2 (2×20 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (50:50 hept-EA) gave the title compound as a yellow oil: TLC:rf (50:50 hept-EA)=0.31. LC-MS-conditions 02: tR=0.82 min.

Workup

extractionThe mixture was extracted with CH2Cl2 (2×20 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (50:50 hept-EA)

Sources & evidence

ORD record: ord-ff4d8f4eec4f4a1a8e81e98c05a23c10
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Reaction notes

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