Potassium Carbonate → HCID 66765542, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]1([CH2:21][OH:22])[CH2:20][O:19][CH2:18]1>C(#N)C>[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:16][C:17]2([CH2:21][OH:22])[CH2:20][O:19][CH2:18]2)[CH:8]=1)([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
4-nitro-1H-pyrazole (0.5 g, 4.42 mmol) and K2CO3 (1.22 g, 8.84 mmol) were suspended in acetonitrile (30 mL) in a 2-necked flask under nitrogen and (3-(bromomethyl)oxetan-3-yl)methanol (1.36 g, 7.52 mmol) was added dropwise. The reaction was heated at 60° C. for 16 h and the solution was concentrated to about ⅓ of the volume under vacuum and then partitioned between DCM (50 mL) and water (50 mL). The organics were dried over Na2SO4, filtered and the solvent evaporated to give (3-((4-nitro-1H-pyrazol-1-yl)methyl)oxetan-3-yl)methanol as a transparent oil (0.94 g, quantitative yield).
Workup
- concentrationthe solution was concentrated to about ⅓ of the volume under vacuum
- custompartitioned between DCM (50 mL) and water (50 mL)
- dry with materialThe organics were dried over Na2SO4
- filtrationfiltered
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-69fa31ec63994d38aaeada247a5c43d3
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040545B2
Reaction notes
Loading…