Dimethylformamide → 1-Methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

HRID 918317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918317
[CH3:1][O:2][C:3]([CH3:13])([CH3:12])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:11])[CH2:8][CH:9]=O.[CH:14]([O-:17])([CH3:16])[CH3:15].[Na+].CN(C)[CH:21]=[O:22]>>[CH3:1][O:2][C:3]([CH3:13])([CH3:12])[CH2:4][CH2:5][CH2:6][CH:7]([CH3:11])[CH2:8][CH:9]=[CH:12][C:3]([CH3:13])=[CH:4][C:21]([O:17][CH:14]([CH3:16])[CH3:15])=[O:22]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 192237-Methoxy-3,7-DimethyloctanalHCID 109204432-Propanol, sodium salt (1:1)

Produkt 1

HCID 385321-Methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate

Versuchsvorschrift

To a mixture of 10 g. of 7-methoxy-3,7-dimethyloctan-1-al, 17 g. of diethyl 3-ethoxycarbonyl-2-methylprop-2-enyl phosphonate (77% trans), and 150 ml. of dimethylformamide, under nitrogen, 0°, with stirring, is added sodium isopropanolate (prepared from 1.5 g. of sodium in 150 ml. of isopropanol). After addition is complete, the reaction is stirred for 18 hours at room temperature and then worked up by extraction with hexane to yield isopropyl 11-methoxy-3,7,11-trimethyldodeca-2,4-dienoate (mostly trans-2,trans-4), which can be chromatographed and distilled for further purification.

Aufarbeitung

  1. additionTo a mixture of 10 g
  2. additionAfter addition
  3. extractionworked up by extraction with hexane

Quellen und Nachweise

ORD-Eintrag
ord-20a9042dbab44d5ea5cfb8cc859f5e06
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03970704

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