Cesium carbonate → 1-(5-(Hydroxymethyl)-3-nitro-1H-pyrazol-1-yl)-2-methylpropan-2-ol

HRID 407746Notes

Reaction equation

HRID 407746 reaction equation
[N+:1]([C:4]1[CH:8]=[C:7]([CH2:9][OH:10])[NH:6][N:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:17][C:18]1([CH3:21])[CH2:20][O:19]1>>[OH:10][CH2:9][C:7]1[N:6]([CH2:17][C:18]([CH3:21])([OH:19])[CH3:20])[N:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 11208Isobutylene oxideHCID 178526711HCID 178526711, compound

Product 1

HCID 866840171-(5-(Hydroxymethyl)-3-nitro-1H-pyrazol-1-yl)-2-methylpropan-2-olYield 38%

Conditions

Temperature
70 °C

Procedure

A sealed tube was charged with 139a (2.145 g, 15 mmol), Cs2CO3 (978 mg, 3.0 mmol), and 2,2-dimethyloxirane (15 mL). The mixture was stirred at 70° C. for 3 h. After cooled to room temperature, the mixture was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (5:1 to 1:1) to afford 139b (1.2 g, 38%) as a white solid. MS-ESI: [M+H]+ 216.2

Workup

  1. temperatureAfter cooled to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica-gel column chromatography
  4. washeluting with petroleum ether/ethyl acetate (5:1 to 1:1)

Sources & evidence

ORD record
ord-736e44ca9d904f9aa45289bd01bd070a
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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