[4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]methanol → 4-Nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-5-carbaldehyde
Reaction equation
[N+:1]([C:4]1[CH:8]=[N:7][N:6]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:5]=1[CH2:17][OH:18])([O-:3])=[O:2]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[N+:1]([C:4]1[CH:8]=[N:7][N:6]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[C:5]=1[CH:17]=[O:18])([O-:3])=[O:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of [4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]methanol (7.776 g, 28.38 mmol) in chloroform (500 mL) was added manganese dioxide (29.18 g, 9 eq). The resulting mixture was heated at reflux for 4 hours, cooled to room temperature and stirred overnight. The reaction mixture was again heated to reflux for 3 hours, filtered through a 3 cm plug of celite using additional chloroform. The filtrate was concentrated to give 4.55 g of crude material and purified via silica gel chromatography with a 2-4% ethyl acetate in hexanes gradient to give the title compound as a colorless oil (1.55 g). M+=271
Workup
- temperatureThe resulting mixture was heated
- temperatureat reflux for 4 hours
- temperatureThe reaction mixture was again heated
- temperatureto reflux for 3 hours
- filtrationfiltered through a 3 cm plug of celite
- concentrationThe filtrate was concentrated
- customto give 4.55 g of crude material
- custompurified via silica gel chromatography with a 2-4% ethyl acetate in hexanes gradient
Sources & evidence
- ORD record
- ord-c75bed4d160c4bcca5b13a1eaf67fb56
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07435731B2
Reaction notes
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