Nitrogen → (5-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)furan-2-yl)methanol

HRID 42739Notes

Reaction equation

N#N.C[O:4][C:5]([C:7]1[O:8][C:9]([CH2:12][N:13]2[N:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[N:14]2)=[CH:10][CH:11]=1)=O.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.C1(C)C=CC=CC=1>[N+:18]([C:16]1[CH:15]=[N:14][N:13]([CH2:12][C:9]2[O:8][C:7]([CH2:5][OH:4])=[CH:11][CH:10]=2)[N:17]=1)([O-:20])=[O:19]

Participants

Conditions

Temperature: -10 °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-carboxylic acid methyl ester (325 mg, 1.28 mmol) in THF (13.0 mL) was treated dropwise, at −10° C. with DiBAL (4.36 mL of a 1M solution in toluene, 4.36 mmol). The reaction mixture was stirred at −10° C. for 1 h followed by 1 h at rt. Sat. aq. Rochelle's salt (40 mL) was added and the reaction mixture was stirred for 1 h at rt. The aq. layer was extracted with EA (2×30 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: TLC:rf (50:50 hept-EA)=0.28. LC-MS-conditions 02: tR=0.77 min.

Workup

waitfollowed by 1 h at rt
stirringthe reaction mixture was stirred for 1 h at rt
extractionThe aq. layer was extracted with EA (2×30 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-ddf7d1f4a64941a98ee522d46029ed5f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Reaction notes

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