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

HRID 1381377
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1381377
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 10928Ethyl chloroformateHCID 13893921HCID 13893921, Verbindung

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8471
Triethylamine
Lösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5fc9bdd734e04850afee00476bfd2dfe
Quelldatensatz
uspto-grants-1986_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04585789

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