Hydrochloric Acid → 2-(6-m-Methoxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione

HRID 1077145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1077145
C(N(CC)[CH2:4][CH2:5][C:6](=[O:18])[CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)C.[CH3:21][CH:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28].[Na].Cl>CO.[Cl-].[Na+].O.CCOCC>[CH3:17][O:16][C:12]1[CH:11]=[C:10]([CH2:9][CH2:8][CH2:7][C:6](=[O:18])[CH2:5][CH2:4][C:22]2([CH3:21])[C:26](=[O:27])[CH2:25][CH2:24][C:23]2=[O:28])[CH:15]=[CH:14][CH:13]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 130052-Methyl-1,3-cyclopentanedioneHCID 5360545SodiumHCID 214855041-(Diethylamino)-6-(3-methoxyphenyl)hexan-3-one

Produkt 1

HCID 203500022-(6-m-Methoxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Add the crude methiodide of 1-diethylamino-6-m-methoxyphenylhexan-3-one (2.5 g) in methanol (10 cc) ice-cold to a solution obtained by adding 2-methylcyclopentane-1,3-dione (0.5 g) to an ice-cold solution of sodium (0.21 g) in methanol (10 cc). Allow the reaction mixture to warm to room temperature and leave for 16 hours, after which add N hydrochloric acid (10 cc) and saturated brine (100 cc), ether-extracting the solution. Evaporate the washed and dried extracts to obtain crude 2-(6-m-methoxyphenyl-3-oxohexyl)-2-methylcyclopentane-1,3-dione as a gum; dissolve in benzene (25 cc) containing toluene-p-sulfonic acid (0.4 g) and reflux the mixture for one hour. Cool, add ether (25 cc), and wash, dry, and evaporate the solution. Take up the resulting gum in benzene (5 cc) and adsorb on a column of Fuller's earth (100 g). Elute with a mixture of benzene and light petroleum to obtain a series of fractions, one of which crystallizes (0.04 g). Boil this fraction with methanol and decant the solution from insoluble oil which forms. Reduce the solution in bulk by evaporation, depositing crystals on cooling; recrystallize from methanol to obtain 13β-methyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-one, m.p. 111°-113°C; ultraviolet absorption peak at 312 mμ (ε34,800).

Aufarbeitung

  1. customobtained
  2. customleave for 16 hours
  3. extractionextracting the solution
  4. customEvaporate the
  5. washwashed
  6. customdried extracts

Quellen und Nachweise

ORD-Eintrag
ord-5f9880a9c4f0417798e1b1e26a5ac893
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03959322

Notizen zur Reaktion

Wird geladen…