Ammonium Chloride → 1-phenyl-5-(1-phenyl-1H-pyrazol-5-yl)penta-1,4-diyn-3-ol
Reaction equation
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][CH:4]=1)#[CH:2].C([Li])CCC.[C:19]1([C:25]#[C:26][CH:27]=[O:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>C1COCC1>[C:19]1([C:25]#[C:26][CH:27]([OH:28])[C:2]#[C:1][C:3]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:6]=[CH:5][CH:4]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1Participants
6
Procedure
To a solution of 5-ethynyl-1-phenyl-1H-pyrazole (0.500 g) in THF (20.0 mL) was added dropwise 2.5M butyllithium in THF solution (1.55 mL) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added dropwise a solution of 3-phenylprop-2-ynal (0.464 g) in THF (5.00 mL) at −78° C., the mixture was stirred for 45 min, and saturated aqueous ammonium chloride solution (10.0 mL) was added. The mixture was extracted with dichloromethane, the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol) to give the title compound (0.73 g).
Workup
- stirringthe mixture was stirred for 45 min
- extractionThe mixture was extracted with dichloromethane
- washthe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (dichloromethane/methanol)
Sources & evidence
- ORD record
- ord-7d57d89db4b845bc934a381b30beb8c2
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150588B2
Reaction notes
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