Sodium Chloride → (Z)-1,2,3-trimethoxy-5-(4-methoxy-3-nitrostyryl)benzene

HRID 260091

Reaktionsgleichung

Reaktionsgleichung von HRID 260091
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH:7]=O)([O-:3])=[O:2].[Br-].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:40]=[C:41]([O:45][CH3:46])[C:42]=1[O:43][CH3:44])[CH2:20]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].[Cl-].[Na+]>C1C=CC=CC=1.C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6](/[CH:7]=[CH:20]\[C:19]2[CH:40]=[C:41]([O:45][CH3:46])[C:42]([O:43][CH3:44])=[C:17]([O:16][CH3:15])[CH:18]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])([O-:3])=[O:2]

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 7006084-Methoxy-3-nitrobenzaldehydeHCID 178418302HCID 178418302, Verbindung

Produkt 1

HCID 10617491(Z)-1,2,3-trimethoxy-5-(4-methoxy-3-nitrostyryl)benzeneAusbeute 43,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

1.54 g of 3-nitro-4-methoxybenzaldehyde and 4.45 g of 3,4,5-trimethoxybenzyltriphenylphosphine bromide were dissolved in 40 ml of benzene, and a benzene solution containing 408 mg of sodium hydride dispersed therein was added thereto and reacted for 15 hours at room temperature (about 20°-30° C.). The reaction mixture was neutralized with acetic acid, saturated sodium chloride solution was added thereto, and the resulting liquid was extracted with dichloromethane. The extract was dried with anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography (ethyl acetate:hexane=1:2 by volume) to obtain 1.27 g of the intended compound. The yield of the product was 43%.

Aufarbeitung

  1. additiondispersed
  2. additiontherein was added
  3. customreacted for 15 hours at room temperature (about 20°-30° C.)
  4. additionwas added
  5. extractionthe resulting liquid was extracted with dichloromethane
  6. dry with materialThe extract was dried with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography (ethyl acetate:hexane=1:2 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-e7bc58f006fb4be784d38370b9d81678
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05525632

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