3,4,5-Trimethoxybenzaldehyde → 2,2-Dimethyl-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]-3(2H)-furanone

HRID 359356Notes

Reaction equation

HRID 359356 reaction equation
[CH3:1][C:2]1([CH3:9])[C:6](=[O:7])[CH:5]=[C:4]([CH3:8])[O:3]1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH:15]=O.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1([CH3:9])[C:6](=[O:7])[CH:5]=[C:4]([CH:8]=[CH:15][C:14]2[CH:17]=[C:18]([O:22][CH3:23])[C:19]([O:20][CH3:21])=[C:12]([O:11][CH3:10])[CH:13]=2)[O:3]1

Participants

5

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 14798Sodium HydroxideHCID 1370803(2H)-Furanone, 2,2,5-trimethyl-

Product 1

HCID 537161062,2-Dimethyl-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]-3(2H)-furanoneYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2,2,5-trimethyl-3(2H)-furanone (2.5 g, 19.8 mM) and 3,4,5-trimethoxybenzaldehyde (4.7 g, 23.8 mM) in ethanol was added 1N aqueous sodium hydroxide (4 mL, 4mM). After the reaction mixture was stirred for 48 hours at room temperature, the solution was concentrated to 50 mL and diluted with water (300 mL). The aqueous layer was extracted with diethyl ether (4×100 mL). The combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford a dark yellow crystalline solid. The crude product was purified by chromatography (silica gel, petroleum ether-ethyl acetate) to give light yellow crystals (5.0 g, 83% yield), m.p. 149°-150° C.

Workup

  1. concentrationthe solution was concentrated to 50 mL
  2. additiondiluted with water (300 mL)
  3. extractionThe aqueous layer was extracted with diethyl ether (4×100 mL)
  4. washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford a dark yellow crystalline solid
  9. customThe crude product was purified by chromatography (silica gel, petroleum ether-ethyl acetate)

Sources & evidence

ORD record
ord-35d8c43986d044b590463d0e55aa15d7
Source dataset
uspto-grants-1991_03
Patent number
US05001126

Reaction notes

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