Diethyl Ether → 2,2-Dimethyl-4-(1-naphthyl)-7-chromanol

HRID 224928

Reaktionsgleichung

Reaktionsgleichung von HRID 224928
[CH3:1][Li].[OH:3][C:4]1C=C2[C:7]([CH:8]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[CH2:9]C(=O)O2)=[CH:6][CH:5]=1.[CH3:25][CH2:26][O:27][CH2:28][CH3:29]>C(O)(=O)C>[CH3:25][C:26]1([CH3:1])[CH2:9][CH:8]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:7]2[C:28](=[CH:29][C:4]([OH:3])=[CH:5][CH:6]=2)[O:27]1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 205705223,4-Dihydro-7-hydroxy-4-(1-naphthyl)coumarinHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 205705012,2-Dimethyl-4-(1-naphthyl)-7-chromanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl-lithium in ether (120 ml., 1.9 M solution) at room temperature was added over 0.5 hours finely powdered 3,4-dihydro-7-hydroxy-4-(1-napthyl) coumarin (14.5 g, 0.05 moles). After refluxing for 1 hour a purple solid precipitated out of solution and the reaction mixture was allowed to cool, acidified with dilute hydrochloric acid and extracted with ether (3×). The combined ether extracts were dried and removal of solvent gave a dark coloured oil which was refluxed overnight in glacial acetic acid. The glacial acetic acid was removed in vacuo and the residue dissolved in ether, washed with water, saturated sodium bicarbonate solution and dried. Removal of solvent gave an extremely viscous oil, column chromatography of which on silica, eluting with 40°-60° petrol: ether (gradually increasing concentration of ether) gave the required chroman as a low melting pale yellow solid (9.4 g., 76%).

Aufarbeitung

  1. temperatureAfter refluxing for 1 hour a purple solid
  2. customprecipitated out of solution
  3. temperatureto cool
  4. extractionextracted with ether (3×)
  5. dry with materialThe combined ether extracts were dried
  6. customremoval of solvent
  7. customgave a dark coloured oil which
  8. customThe glacial acetic acid was removed in vacuo
  9. dissolutionthe residue dissolved in ether
  10. washwashed with water, saturated sodium bicarbonate solution
  11. customdried
  12. customRemoval of solvent
  13. customgave an extremely viscous oil, column chromatography of which on silica
  14. washeluting with 40°-60° petrol
  15. temperatureether (gradually increasing concentration of ether)

Quellen und Nachweise

ORD-Eintrag
ord-9cae920ddb7d484d8d9ca5cc6f7799b8
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04234726

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