HCID 178418486, compound → HCID 178450381, compound
Reaction equation
[C:1]([Mg]Br)#[CH:2].[NH:5]1[CH:9]=[N:8][C:7]([C:10](=[O:12])[CH3:11])=[N:6]1>C1COCC1>[NH:5]1[CH:9]=[N:8][C:7]([C:10]([OH:12])([C:1]#[CH:2])[CH3:11])=[N:6]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
This compound was prepared according to a procedure similar to that described in Procedure A. Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed ethynylmagnesium bromide (45 mL, 2.50 equiv). This was followed by the addition of a solution of 1-(1H-1,2,4-triazol-3-yl)ethan-1-one (1000 mg, 9.00 mmol, 1.00 equiv) in THF (2 mL) dropwise with stirring at 0° C. The resulting solution was stirred for 10 min at 0° C. The resulting solution was allowed to react with stiffing for an additional 6 h at room temperature. The reaction was then quenched by the addition of 10 mL of sat. aq. NH4Cl. The resulting solution was extracted with 2×50 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with petroleum ether:ethyl acetate (1:1). This resulted in 0.4 g (32%) of 2-(1H-1,2,4-triazol-3-yl)but-3-yn-2-ol as a white solid.
Workup
- customThis compound was prepared
- customInto a 100-mL 3-necked round-bottom flask purged
- temperaturemaintained with an inert atmosphere of nitrogen
- stirringThe resulting solution was stirred for 10 min at 0° C
- customto react
- customThe reaction was then quenched by the addition of 10 mL of sat. aq. NH4Cl
- extractionThe resulting solution was extracted with 2×50 mL of ethyl acetate
- dry with materialdried over anhydrous sodium sulfate
- customThis resulted in 0.4 g (32%) of 2-(1H-1,2,4-triazol-3-yl)but-3-yn-2-ol as a white solid
Sources & evidence
- ORD record
- ord-7ae1d41508a743bb893e528fbddabf1c
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034866B2
Reaction notes
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