1,4-Dioxane → 5-Hydroxy-4-([3,4-methylenedioxyphenyl]methyl)-2(5H)-furanone

HRID 1494426Notes

Reaction equation

HRID 1494426 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.Cl.N1CCCCC1.O1CCOCC1.[CH2:20]1[O:28][C:27]2[CH:26]=[CH:25][C:24]([CH2:29][CH2:30][CH:31]=[O:32])=[CH:23][C:22]=2[O:21]1>O>[OH:32][CH:31]1[O:6][C:2](=[O:5])[CH:3]=[C:30]1[CH2:29][C:24]1[CH:25]=[CH:26][C:27]2[O:28][CH2:20][O:21][C:22]=2[CH:23]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 1692031,3-Benzodioxole-5-propanalHCID 2723721Piperidine, hydrochloride (1:1)HCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 147509095-Hydroxy-4-([3,4-methylenedioxyphenyl]methyl)-2(5H)-furanoneYield 28.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.5 g (0.027 mol) of glyoxylic acid hydrate, 3.2 g (0.027 mol) of piperidine hydrochloride, and 30 mL of dioxane were mixed with stirring, whereupon water was added in dropwise fashion until a homogeneous solution resulted. 3-(3,4-Methylenedioxyphenyl)propionaldehyde (4.8 g, 0.027 mol) was then introduced and the solution allowed to stir at room temperature for 1 hour, then heated at reflux for 48 hours. At the end of this time the solution was concentrated, diluted with water, and extracted with EtOAc (2×100 mL). The organic layer was separated, dried (MgSO4) then concentrated to afford an oil. The crude oil was chromatographed over silica gel (150 g). Elution with 50% EtOAc-hexane afforded 1.8 g, 28% of the desired product as a light yellow oil.

Workup

  1. additionwas added in dropwise fashion until a homogeneous solution
  2. customresulted
  3. temperatureheated
  4. temperatureat reflux for 48 hours
  5. concentrationAt the end of this time the solution was concentrated
  6. additiondiluted with water
  7. extractionextracted with EtOAc (2×100 mL)
  8. customThe organic layer was separated
  9. dry with materialdried (MgSO4)
  10. concentrationthen concentrated
  11. customto afford an oil
  12. customThe crude oil was chromatographed over silica gel (150 g)
  13. washElution with 50% EtOAc-hexane

Sources & evidence

ORD record
ord-0f46d3482e0346c89a02d41db77629c2
Source dataset
uspto-grants-1991_06
Patent number
US05026725

Reaction notes

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