3,4-Dimethoxybenzophenone → 1-(3,4-Dimethoxyphenyl)-1-phenylprop-1-ene

HRID 583442

Reaktionsgleichung

Reaktionsgleichung von HRID 583442
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:17]2[CH:22]=[CH:21][C:20](OC)=[C:19](OC)[CH:18]=2)=[CH:12][C:13](OC)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].COC1C=C(C=CC=1OC)C(C1C=CC=CC=1)=O.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:12][CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

5

Edukt 3

HCID 2867423,4-DimethoxybenzophenoneHCID 2733832Lithium HexamethyldisilazideHCID 9820154Methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylate

Produkt 1

HCID 541210301-(3,4-Dimethoxyphenyl)-1-phenylprop-1-ene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Katalysator

Versuchsvorschrift

1-(3,4-Dimethoxyphenyl)-1-phenylprop-1-ene was prepared analogously to methyl 3,3-bis-(3,4-dimethoxyphenyl)acrylate using 3,4-dimethoxybenzophenone (3 g, 12.4 mmol), (ethyl)triphenylphosphonium bromide (5.1 g, 13.6 mmol) and lithium hexamethyldisilazide (13.6 mL, 13.6 mmol, 1M) with a reaction time of 4 hours at room temperature. The crude mixture was purified by flash column chromatography (silica gel, 10% hexane/methylene chloride) to afford 1.3 g (41%) of a mixture of the E and Z isomers as a white solid: mp 72-73° C.; 1H NMR (CDCl3) δ 7.40-6.80 (m, 16H), 6.16-6.08 (m, 2H), 3.90-3.80 (m, 12H), 1.97-1.73 (m, 6H); 13C NMR (CDCl3) δ 148.6, 148.5, 148.1, 147.8 142.9, 142.3, 142.0, 140.0, 136.0, 132.5, 129.9, 128.0, 128.0, 127.1, 126.7, 126.6, 123.8, 122.6, 122.5, 119.8, 113.6, 110.8, 110.7, 110.4, 55.8, 55.8, 55.7, 15.7, 15.5; Anal. Calcd for C17H18O2. Theoretical: C, 80.28; H, 7.13. Found: C, 79.94; H, 7.12.

Aufarbeitung

  1. customwith a reaction time of 4 hours
  2. customat room temperature
  3. customThe crude mixture was purified by flash column chromatography (silica gel, 10% hexane/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-e40011a9137549aeafc379b4596895ba
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929117

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