2-Hexanone → HCID 12081746, compound

HRID 1978278Notes

Reaction equation

HRID 1978278 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11]N=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:26][C:27](=O)[CH2:28][CH2:29][CH2:30][CH3:31].CC1C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(O)=O.[Na+]>C1COCC1.CCOCC>[CH3:10][O:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[NH:11][C:27]([CH3:26])=[C:28]2[CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 115832-HexanoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 12081745HCID 12081745, compound

Product 1

HCID 12081746HCID 12081746, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(3,4-Dimethoxyphenyl)-benzophenone hydrazone (1.0 equiv., 0.32 mmol, 105 mg), 2-hexanone (5 equiv., 1.58 mmol, 0.19 mL), and TsOH.H2O (10 equiv., 3.2 mmol, 609 mg) were dissolved in THF (10 mL) and heated to reflux for 67 hours. The reaction mixture was then cooled to room temperature, diluted with Et2O (5 mL), neutralized with a saturated NaHCO3 solution, and extracted with Et2O (3×10 mL). The organic extracts were then dried over K2CO3, filtered and concentrated under vacuum. Purification by flash column chromatography (20% EtOAc/Hex) gave the title product as a yellow oil (60 mg, 0.26 mmol, 80% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 67 hours
  3. extractionextracted with Et2O (3×10 mL)
  4. dry with materialThe organic extracts were then dried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by flash column chromatography (20% EtOAc/Hex)

Sources & evidence

ORD record
ord-7750c8d99b8c4030b0872bd8057f3f71
Source dataset
uspto-grants-2001_05
Patent number
US06235936B1

Reaction notes

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