Sodium Cyanide → 1-(3-Iodo-5-methoxy-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione

HRID 1085632

Reaktionsgleichung

Reaktionsgleichung von HRID 1085632
[I:1][C:2]1[C:3]([O:12][CH2:13][CH2:14][CH3:15])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C-]#N.[Na+].CN(C)[CH2:21][CH2:22][C:23]([C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1)=[O:24]>CN(C=O)C>[I:1][C:2]1[C:3]([O:12][CH2:13][CH2:14][CH3:15])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([C:7](=[O:8])[CH2:21][CH2:22][C:23]([C:25]2[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[C:29]([O:31][CH3:32])[CH:30]=2)=[O:24])[CH:9]=1

Komponenten

5

Edukt 3

HCID 8929Sodium CyanideHCID 4123063-(Dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-oneHCID 47701013-Iodo-5-methoxy-4-propoxybenzaldehyde

Produkt 1

HCID 157180281-(3-Iodo-5-methoxy-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of 5-iodo 3-methoxy-4-n-propoxybenzaldehyde (26 g, 0.08 mol) in DMF (75 ml) was added over 15 minutes to a stirred solution of sodium cyanide (4 g, 0.08 mol) in DMF (100 ml) at 35° C. After stirring for 20 minutes, a solution of 3-dimethylamino-1-(3,4,5-trimethoxyphenyl)-1-propanone (18 g, 0.07 mol) in DMF (100 ml) was added over 0.5 hour. The mixture was stirred at 35° C. for 1 hour and kept at room temperature overnight. It was poured into ice-cold 20% hydrochloric acid (2 1), and the solid was filtered, dried by suction, and taken up in ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and the filtrate was evaporated to dryness. Crystallization from Et2O-hexane gave 1-(5-iodo-3-methoxy-4-n-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione, m.p. 120°-121° C.

Aufarbeitung

  1. stirringThe mixture was stirred at 35° C. for 1 hour
  2. waitkept at room temperature overnight
  3. filtrationthe solid was filtered
  4. customdried by suction
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated to dryness
  8. customCrystallization from Et2O-hexane

Quellen und Nachweise

ORD-Eintrag
ord-27d1b38fc75848e2af2e078b3e9a6f68
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05010100

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