2,5-Hexanedione → HCID 71272748, compound

HRID 475078Notes

Reaction equation

HRID 475078 reaction equation
[CH3:1][Si:2]([CH3:14])([CH3:13])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][C:9]([NH2:12])=[N:8]1.[CH3:15][C:16](=O)[CH2:17][CH2:18][C:19](=O)[CH3:20]>CC1C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:20][C:19]1[N:12]([C:9]2[CH:10]=[CH:11][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:14])([CH3:13])[CH3:1])[N:8]=2)[C:16]([CH3:15])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 80352,5-HexanedioneHCID 57562604HCID 57562604, compound

Product 1

HCID 71272748HCID 71272748, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

Into a 2 L round-bottom flask under nitrogen was placed 1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazol-3-amine (110 g, 515.58 mmol, 1.00 equiv.), toluene (1.2 L), hexane-2,5-dione (60.0 g, 525.66 mmol, 1.00 equiv.), and 4-methylbenzene-1-sulfonic acid (1.0 g, 5.81 mmol, 0.10 equiv.). The resulting solution was heated to reflux for 2 h, cooled and concentrated under vacuum. The residue was purified by SiO2 chromatography eluting with EtOAc/petroleum ether (1:50) to afford 3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole (132 g, 83%) as a light yellow solid.

Workup

  1. customInto a 2 L round-bottom flask under nitrogen was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 2 h
  4. temperaturecooled
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by SiO2 chromatography
  7. washeluting with EtOAc/petroleum ether (1:50)

Sources & evidence

ORD record
ord-75bd11b363404cc892a29b4164604393
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

Loading…