Phosphoric Acid → 4,5-Dimethyl-3-hydroxy-2,5-dihydro-2-furanone, (+)-

HRID 2399605Notes

Reaction equation

HRID 2399605 reaction equation
[Na].[O:2]=[C:3]([CH:7]([CH3:11])[CH:8]([OH:10])[CH3:9])[C:4](O)=[O:5].P(=O)(O)(O)O>O>[OH:2][C:3]1[C:4](=[O:5])[O:10][C@@H:8]([CH3:9])[C:7]=1[CH3:11]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 5360545SodiumHCID 19386107HCID 19386107, compound

Product 1

HCID 53259214,5-Dimethyl-3-hydroxy-2,5-dihydro-2-furanone, (+)-Yield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

840 mg of the sodium salt of compound I were dissolved in 50 ml of H2O and brought to pH 2.0 with dilute phosphoric acid. The solution was held at 85° C. for 30 minutes and, after cooling, extracted with 2×50 ml of ethyl acetate. 320 mg (yield 50%) of compound III separated after removal of the solvent. Compound III, purified by preparative thin-layer chromatography (silica gel 60), exhibited an optical rotation of: [α]D20 : 21.66° (c 1.0 in chloroform).

Workup

  1. temperatureafter cooling
  2. extractionextracted with 2×50 ml of ethyl acetate

Sources & evidence

ORD record
ord-49b3bf86766d415cb1a80ab0282af004
Source dataset
uspto-grants-1995_09
Patent number
US05449823

Reaction notes

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