Dimethylformamide → Ethyl 11-mercapto-3,7,11-trimethyldodeca-2,4-dienoate

HRID 1605139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1605139
[SH:1][C:2]([CH3:12])([CH3:11])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:10])[CH2:7][CH:8]=O.[CH2:13]([O:15][C:16]([CH:18]=[C:19]([CH3:31])[CH2:20]P(=O)(OC(C)C)OC(C)C)=[O:17])[CH3:14].CN(C)C=O.[OH-].[Na+]>CCCCCC.O>[SH:1][C:2]([CH3:11])([CH3:12])[CH2:3][CH2:4][CH2:5][CH:6]([CH3:10])[CH2:7][CH:8]=[CH:20][C:19]([CH3:31])=[CH:18][C:16]([O:15][CH2:13][CH3:14])=[O:17]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 215493457-Mercapto-3,7-dimethyloctan-1-alHCID 54005430Ethyl 4-(diisopropoxy-phosphoryl)-3-methylbut-2-enoate

Produkt 1

HCID 54474469Ethyl 11-mercapto-3,7,11-trimethyldodeca-2,4-dienoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22114717Water hexaneLösungsmittel

Versuchsvorschrift

A mixture of 5 g. of 7-mercapto-3,7-dimethyloctan-1-al 8.5 g. of di-isopropyl 3-ethoxycarbonyl-2-methylprop-2-enyl-phosphonate, and 40 ml. of dimethylformamide, under nitrogen and cooled in an ice-bath, is stirred for 0.5 hours and then ground NaOH (1.165g.) is added. The reaction mixture is stirred at room temperature for 3 hours and then hexane-water (1/1) added. The organic layer is washed with water and brine, dried over calcium sulfate and concentrated. The concentrate is filitered through Florisil using hexane and hexane/ether. The filtrate is concentrated and then distilled to yield ethyl 11-mercapto-3,7,11-trimethyldodeca-2,4 -dienoate (mostly trans-2, trans-4).

Aufarbeitung

  1. additionA mixture of 5 g
  2. additionis added
  3. stirringThe reaction mixture is stirred at room temperature for 3 hours
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over calcium sulfate
  6. concentrationconcentrated
  7. concentrationThe filtrate is concentrated
  8. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-139c9eed1963451d8d8a53c2cb1214f9
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03948996

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