Potassium Carbonate → HCID 13710167, compound

HRID 1854682Notes

Reaction equation

HRID 1854682 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([OH:12])[CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[C:23]([CH3:25])[CH3:24]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:13]([N:3]([CH2:1][CH3:2])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([O:12][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH:5]=1)[CH3:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 872934-(Diethylamino)-2-hydroxybenzaldehyde

Product 1

HCID 13710167HCID 13710167, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-diethylamino-2-hydroxybenzaldehyde (300 mg, 1.55 mmol), potassium carbonate (428 mg, 3.10 mmol), and tetrabutylammonium iodide (57 mg, 0.15 mmol) in 1.6 mL of dry N,N-dimethylformamide was added prenyl bromide (0.27 mL, 2.3 mmol) at 0° C. After being stirred at room temperature for 7 h, the reaction mixture was filtered to remove inorganic salts. The filtrate was diluted with diethyl ether, and the solution was washed with water, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25) to obtain the title compound as a pale yellow gum (377 mg, 93%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto remove inorganic salts
  3. additionThe filtrate was diluted with diethyl ether
  4. washthe solution was washed with water, saturated NaHCO3 aqueous solution, brine
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25)

Sources & evidence

ORD record
ord-fb3ae6347b1647918ab2cf21549aac83
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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