Hydrochloric Acid → Ethyl 7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2,2-dimethyl-7-phenylheptanoate

HRID 1646824

Reaktionsgleichung

Reaktionsgleichung von HRID 1646824
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[CH:14]([CH3:16])[CH3:15].I[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:33]1[C:38]([CH3:39])=[C:37]([O:40][CH3:41])[C:36]([CH3:42])=[C:35]([CH3:43])[C:34]=1[O:44][CH3:45])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl.C(OC(C)C)(C)C.[Cl-].[Na+]>O1CCCC1.CCCCCC>[CH3:45][O:44][C:34]1[C:35]([CH3:43])=[C:36]([CH3:42])[C:37]([O:40][CH3:41])=[C:38]([CH3:39])[C:33]=1[CH:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:25][CH2:24][CH2:23][CH2:22][C:14]([CH3:16])([CH3:15])[C:13]([O:18][CH2:19][CH3:20])=[O:17]

Komponenten

10

Edukt 7

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7342Ethyl isobutyrateHCID 7912DiisopropylamineHCID 7914Diisopropyl EtherHCID 190880841-Iodo-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-phenylpentaneHCID 178418339Butyllithium

Produkt 1

HCID 19088026Ethyl 7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2,2-dimethyl-7-phenylheptanoateAusbeute 247,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A 2.1 ml (3.0×1.1 mmole) portion of n-butyllithium. hexane solution was added dropwise to a solution of 0.50 ml (3.0×1.2 mmole) of diisopropylamine in anhydrous tetrahydrofuran (5 ml) under an atmosphere of argon at -20° C. over the period of 5 minutes, followed by stirring at -20° to -5° C. for 10 minutes. The mixed solution was cooled at -20° C. and a solution of 0.38 g (3.0×1.1 mmole) of ethyl isobutyrate in tetrahydrofuran (4 ml) was added dropwise to it over the period of 5 minutes, followed by stirring at -20° to -5° C. for 20 minutes. A solution of 1.36 g (3.0 mmole) of 1-iodo-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-phenylpentane in tetrahydrofuran (14 ml) was added dropwise to the mixed solution over the period of 5 minutes, followed by stirring at -20° to -10° C. for 1.5 hours. After the reaction solution was cooled with ice, the reaction was suspended by adding 1N hydrochloric acid, and isopropyl ether and sodium chloride were added to extract the product. The organic layer was separated out, washed with aqueous saturated sodium chloride solution, dried (magnesium sulfate) and evaporated. The residual solution was chromatographed on a silica gel column to perform purification (elution with hexane/isopropyl ether) to thereby give 1.20 g (91%) of ethyl 7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2,2-dimethyl-7-phenylheptanoate. Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 14.

Aufarbeitung

  1. stirringby stirring at -20° to -5° C. for 20 minutes
  2. stirringby stirring at -20° to -10° C. for 1.5 hours
  3. temperatureAfter the reaction solution was cooled with ice
  4. additionwere added
  5. extractionto extract the product
  6. customThe organic layer was separated out
  7. washwashed with aqueous saturated sodium chloride solution
  8. dry with materialdried (magnesium sulfate)
  9. customevaporated
  10. customThe residual solution was chromatographed on a silica gel column
  11. custompurification (elution with hexane/isopropyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-45403bbaadba4679a45ba360d316f1b0
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05180742

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