Water → 4'-Propyl-bicyclohexyl-4-carboxylic acid 3-acryloyloxy-propyl ester

HRID 386327

Reaktionsgleichung

Reaktionsgleichung von HRID 386327
[C:1]([O-:5])(=[O:4])[CH:2]=[CH2:3].[Na+].CC(=C)C(OCCC[CH2:15][CH2:16][CH2:17][O:18][C:19]([CH:21]1[CH2:26][CH2:25][CH:24]([CH:27]2[CH2:32][CH2:31][CH:30]([CH2:33][CH2:34][CH2:35]CC)[CH2:29][CH2:28]2)[CH2:23][CH2:22]1)=[O:20])=O.[I-].[Na+].O>CN(C)C=O>[C:1]([O:5][CH2:15][CH2:16][CH2:17][O:18][C:19]([CH:21]1[CH2:26][CH2:25][CH:24]([CH:27]2[CH2:28][CH2:29][CH:30]([CH2:33][CH2:34][CH3:35])[CH2:31][CH2:32]2)[CH2:23][CH2:22]1)=[O:20])(=[O:4])[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 5238Sodium IodideHCID 4068533Sodium acrylateHCID 592890404'-Pentyl-bicyclohexyl-4-carboxylic acid 6-(2-methyl-acryloyloxy)-hexyl ester

Produkt 1

HCID 592890704'-Propyl-bicyclohexyl-4-carboxylic acid 3-acryloyloxy-propyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of sodium acrylate (2.5 g, 13.4 mmol), 4′-propyl-bicyclohexyl-4-carboxylic acid 3-bromo-propyl ester (synthesis described for preferred example 1) (5.0 g, 13.4 mmol) and sodium iodide (2.5 g, 16.7 mmol) in dimethylformamide (150 ml) is stirred at 130° C. overnight. The mixture is cooled to room temperature, poured into water, and this is extracted twice with diethyl ether. The ethereal solution is washed with water and then dried over sodium sulphate. The solution is evaporated to dryness and purified by flash column chromatography using DCM/petrol (1/1) as eluant to give upon evaporation of the appropriate fractions a colourless oil.

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. extractionthis is extracted twice with diethyl ether
  3. washThe ethereal solution is washed with water
  4. dry with materialdried over sodium sulphate
  5. customThe solution is evaporated to dryness
  6. custompurified by flash column chromatography
  7. customto give upon evaporation of the appropriate fractions a colourless oil

Quellen und Nachweise

ORD-Eintrag
ord-3352ca3e5f3a43e796f555dd60c1a09a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372307B2

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