Acetic Acid → 1-(3,5-Dimethoxyphenyl)-2-methyl-4-phenyl-1-butene

HRID 614117

Reaktionsgleichung

Reaktionsgleichung von HRID 614117
C([Li])CCC.[Br-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:32]=[C:33]([O:35][CH3:36])[CH:34]=1)[CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:37]([CH2:44][C:45](=O)[CH3:46])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(O)(=O)C>O1CCCC1>[CH3:36][O:35][C:33]1[CH:32]=[C:11]([CH:12]=[C:45]([CH3:46])[CH2:44][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:10]=[C:9]([O:8][CH3:7])[CH:34]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 17355Benzyl acetoneHCID 10962038(3,5-Dimethoxybenzyl)triphenylphosphonium bromideHCID 178418339Butyllithium

Produkt 1

HCID 543320961-(3,5-Dimethoxyphenyl)-2-methyl-4-phenyl-1-butene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of n-butyl lithium (29 ml. of 2.2M) is added dropwise to 3,5-dimethoxybenzyl triphenylphosphonium bromide (31.5 g.) in tetrahydrofuran (200 ml.) with stirring and the resulting deep red solution is stirred for one-half hour. Benzyl acetone (9.4 g.) is added dropwise and the reaction mixture stirred for 12 hours. It is then adjusted to pH 7 by addition of acetic acid and concentrated under reduced pressure. The residue is extracted with methylene chloride and the extract evaporated to give crude 1-(3,5-dimethoxyphenyl)-2-methyl-4-phenyl-1-butene as an oil. It is purified by chromatography on silica gel (400 g.) and elution with benzene. Yield: 10 g. as an oil.

Aufarbeitung

  1. stirringthe resulting deep red solution is stirred for one-half hour
  2. stirringthe reaction mixture stirred for 12 hours
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue is extracted with methylene chloride
  5. customthe extract evaporated

Quellen und Nachweise

ORD-Eintrag
ord-db9ce1adce5c49d292d567985b407e48
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04143139

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