Hexane → 1-Tert-butyl-5-iso-butyl-3-formylpyrazole

HRID 1984127Notes

Reaction equation

HRID 1984127 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[C:12]([N:16]1[C:20]([CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:19][C:18]([CH2:25][OH:26])=[N:17]1)([CH3:15])([CH3:14])[CH3:13].CCCCCC.CCOC(C)=O>C(Cl)Cl.CCOCC>[C:12]([N:16]1[C:20]([CH2:21][CH:22]([CH3:23])[CH3:24])=[CH:19][C:18]([CH:25]=[O:26])=[N:17]1)([CH3:14])([CH3:15])[CH3:13]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 68974985HCID 68974985, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 224935831-Tert-butyl-5-iso-butyl-3-formylpyrazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

PCC (0.67 g, 3.12 mmol) and silica gel (0.50 g) were grinded together and dispersed in 10 ml of purified CH2Cl2 followed by treatment with ultrasound at 20° C. for 30 minutes. 1-tert-butyl-5-iso-butyl-3-hydroxymethylpyrazole (0.50 g, 2.08 mmol) was dissolved in 10 ml of purified CH2Cl2 and the solution was added thereto and treated with ultrasound for 15 minutes. The reaction progress and completion were confirmed using TLC (hexane:EtOAc=6:1). Upon completion of the reaction, ether was added to the reaction mixture and then the resulting mixture was filtered through a celite bed, and concentrated under reduced pressure. The concentrate was separated by column chromatography (hexane:EtOAc:CH2Cl2=3:1:1) to obtain the compound of the present invention.

Workup

  1. additionthe solution was added
  2. additiontreated with ultrasound for 15 minutes
  3. additionwas added to the reaction mixture
  4. filtrationthe resulting mixture was filtered through a celite bed
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate was separated by column chromatography (hexane:EtOAc:CH2Cl2=3:1:1)
  7. customto obtain the compound of the present invention

Sources & evidence

ORD record
ord-0a64036bfdd949b29aa4e0c994f0d00b
Source dataset
uspto-grants-2009_06
Patent number
US07544686B2

Reaction notes

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