Water → 2,2-dimethyl-7-(2-dimethylaminoethoxy)-4(6-methoxy-2-naphthyl)-2H-chromene

HRID 1679139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1679139
[CH3:1][C:2]1([CH3:25])[CH:11]=[C:10]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([OH:24])=[CH:7][CH:8]=2)[O:3]1.[H-].[Na+].[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31]Cl.O>C1(C)C=CC=CC=1.CCOCC>[CH3:1][C:2]1([CH3:25])[CH:11]=[C:10]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([O:24][CH2:31][CH2:30][N:29]([CH3:33])[CH3:28])=[CH:7][CH:8]=2)[O:3]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 205704934-(6-Methoxynaphthalen-2-yl)-2,2-dimethyl-2H-1-benzopyran-7-ol

Produkt 1

HCID 205705022,2-dimethyl-7-(2-dimethylaminoethoxy)-4(6-methoxy-2-naphthyl)-2H-chromene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a refluxing solution of 2,2-dimethyl-7-hydroxy-4(6-methoxy-2-naphthyl)2H-chromene (6.4 g, 0.019 mole) and sodium hydride (1.4 g, 80% dispersion in oil) in toluene (150 ml) was added dropwise 2-dimethylaminoethyl chloride (2.7 g, 0.025 mole). After refluxing for 3 hours the solution was cooled and water added. The organic layer was separated and removal of the solvent gave a residue which dissolved in ether and extracted with dilute hydrochloric acid (3x). The combined acid extracts were basified with 40% sodium hydroxide solution and extracted with ether (3x). The combined ether extracts were dried and removal of the solvent gave a quantitative yield of 2,2-dimethyl-7-(2-dimethylaminoethoxy)-4(6-methoxy-2-naphthyl)-2H-chromene which was converted to the hydrochloride salt m.p. 96°-98° C.

Aufarbeitung

  1. temperatureAfter refluxing for 3 hours the solution
  2. temperaturewas cooled
  3. customThe organic layer was separated
  4. customremoval of the solvent
  5. customgave a residue which
  6. extractionextracted with dilute hydrochloric acid (3x)
  7. extractionextracted with ether (3x)
  8. dry with materialThe combined ether extracts were dried
  9. customremoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-b8e740384fad4a5985aa929533fde8c0
Quelldatensatz
uspto-grants-1978_03
Patentnummer
US04079066

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