Potassium Carbonate → 1-(2-hydroxypropyl)-1H-pyrazole-4-carbaldehyde

HRID 220486Notes

Reaction equation

HRID 220486 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]1.Br[CH2:9][CH:10]([OH:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:12][CH:10]([CH3:11])[CH2:9][N:1]1[CH:5]=[C:4]([CH:6]=[O:7])[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 297401-Bromo-2-propanolHCID 51306731H-pyrazole-4-carbaldehyde

Product 1

HCID 875099441-(2-hydroxypropyl)-1H-pyrazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

Combine 1H-pyrazole-4-carbaldehyde (0.150 g, 1.56 mmol), racemic 1-bromo-2-propanol (0.260 g, 1.87 mmol), and potassium carbonate (0.323 g, 2.34 mmol) in acetonitrile (2 mL). Heat in microwave at 150° C. for 20 min. Filter, wash with acetonitrile and concentrate filtrate. Purify via silica gel chromatography, eluting with 0:100 to 100:0 ethyl acetate:hexanes) to give the title preparation (177 mg, 73%). GC-MS: m/z=154 [M+].

Workup

  1. filtrationFilter
  2. washwash with acetonitrile
  3. concentrationconcentrate filtrate
  4. customPurify via silica gel chromatography
  5. washeluting with 0:100 to 100:0 ethyl acetate
  6. customhexanes) to give the title
  7. custompreparation (177 mg, 73%)

Sources & evidence

ORD record
ord-ed4bf177d43f4255acb295070f6f56a9
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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