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

HRID 1089496Notes

Reaction equation

HRID 1089496 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, 4 mM). 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-cc75b70fa5964f96b8683bf08ec91c77
Source dataset
uspto-grants-1990_10
Patent number
US04966905

Reaction notes

Loading…