Ethyl chloroformate → 3-Hydroxy-5-(3-hydroxypropyl)-4-phenylfuran-2(5H)-one

HRID 1381377Notes

Reaction equation

HRID 1381377 reaction equation
[C:1]([O:4][C:5]1[C:9](=[O:10])[O:8][CH:7]([CH2:11][CH2:12][C:13](O)=[O:14])[C:6]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:3])[CH3:2].C(Cl)(=O)OCC>O1CCCC1.C(N(CC)CC)C>[OH:4][C:5]1[C:9](=[O:10])[O:8][CH:7]([CH2:11][CH2:12][CH2:13][OH:14])[C:6]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:1]([O:4][C:5]1[C:9](=[O:10])[O:8][CH:7]([CH2:11][CH2:12][CH2:13][OH:14])[C:6]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 10928Ethyl chloroformateHCID 13893921HCID 13893921, compound

Product 2

HCID 133895803-Hydroxy-5-(3-hydroxypropyl)-4-phenylfuran-2(5H)-oneHCID 138939235-(3-Hydroxypropyl)-2-oxo-4-phenyl-2,5-dihydrofuran-3-yl acetate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-5 °C

Procedure

3-(4-Acetoxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionic acid (58 mg) was dissolved in a mixture of tetrahydrofuran (3 ml) and triethylamine (28 μl), and a solution of ethyl chlorocarbonate (19 μl) in tetrahydrofuran (1 ml) was added dropwise slowly at -5° C. over 10 minutes. The mixture was stirred at -5° C. for 30 minutes and filtered. To the filtrate was added a solution of sodium borohydride (23 mg) in water (1 ml) at 10° C. Then, the mixture was stirred at room temperature for 1.5 hours, acidified with cooled 1N hydrochloric acid, and extracted with ethyl acetate. After drying, the solvent was distilled off, and the residue was subjected to preparative silica gel thin layer chromatography (0.5 mm×4, Merck) using 35% ethyl acetate-chloroform as the developing solvent to give 3-hydroxy-5-(3-hydroxypropyl)-4-phenyl-2(5H)-furanone (Compound I, 10 mg) and 3-acetoxy-5-(3-hydroxypropyl)-4-phenyl-2(5H)-furanone (Compound II, 12 mg).

Workup

  1. filtrationfiltered
  2. additionTo the filtrate was added a solution of sodium borohydride (23 mg) in water (1 ml) at 10° C
  3. stirringThen, the mixture was stirred at room temperature for 1.5 hours
  4. temperaturewith cooled 1N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. customAfter drying
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-5fc9bdd734e04850afee00476bfd2dfe
Source dataset
uspto-grants-1986_04
Patent number
US04585789

Reaction notes

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