Acetylacetone → HCID 71278942, compound

HRID 1750024Notes

Reaction equation

HRID 1750024 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Br[CH2:27][C:28]1[C:36]2[O:35][CH2:34][C:33](=[O:37])[C:32]=2[CH:31]=[CH:30][C:29]=1[O:38][CH3:39]>C1COCC1.O>[CH3:39][O:38][C:29]1[CH:30]=[CH:31][C:32]2[C:33](=[O:37])[CH2:34][O:35][C:36]=2[C:28]=1[CH2:27][CH:4]([C:5](=[O:7])[CH3:6])[C:1](=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 31261AcetylacetoneHCID 2724141Tetrabutylammonium Fluoride2×HCID 86682096HCID 86682096, compound

Product 1

HCID 71278942HCID 71278942, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of acetylacetone (0.100 g, 1.00 mmol) in THF (2.5 mL) was added with a 1 M solution of tetrabutylammonium fluoride in THF (1.00 mL, 1.00 mmol) and water (1 mL), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was added with a solution of 7-(bromomethyl)-6-methoxybenzofuran-3(2H)-one (0.257 g, 1.00 mmol) in THF (2 mL), and the mixture was stirred at room temperature for 16 hours. The reaction mixture was added with a 1 M solution of tetrabutylammonium fluoride in THF (1.00 mL, 1.00 mmol), and the mixture was stirred at room temperature for additional 5 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain 3[(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]pentane-2,4-dione (0.0533 g, 19%).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hours
  2. stirringthe mixture was stirred at room temperature for additional 5 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6adf03922578472e8c66dc05c33421cb
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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