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Ethyl vinyl ether → 15-Chloro-2-(1-ethoxyethoxy)3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrile

HRID 486866
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Reaktionsgleichung

Reaktionsgleichung von HRID 486866
[Cl:1][CH2:2][C:3]([CH3:24])=[CH:4][CH2:5][CH2:6][C:7]([CH3:23])=[CH:8][CH2:9][CH2:10][C:11]([CH3:22])=[CH:12][CH:13]=[C:14]([CH:19]([CH3:21])[CH3:20])[CH:15]([OH:18])[C:16]#[N:17].[CH:25]([O:27][CH2:28][CH3:29])=[CH2:26].C(=O)([O-])O.[Na+].CCCCCC.CCOCC>ClCCl>[Cl:1][CH2:2][C:3]([CH3:24])=[CH:4][CH2:5][CH2:6][C:7]([CH3:23])=[CH:8][CH2:9][CH2:10][C:11]([CH3:22])=[CH:12][CH:13]=[C:14]([CH:19]([CH3:20])[CH3:21])[CH:15]([O:18][CH:25]([O:27][CH2:28][CH3:29])[CH3:26])[C:16]#[N:17]
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Komponenten

6

Edukt 4

HCID 8023Ethyl vinyl etherHCID 516892Sodium BicarbonateHCID 21584099Diethylether hexaneHCID 5450637515-Chloro-2-hydroxy-3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13 pentadecatetraenenitrile

Produkt 1

HCID 5373709415-Chloro-2-(1-ethoxyethoxy)3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrileAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 15-chloro-2-hydroxy-3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrile (204 mg, 0.56 mmol) prepared in Reference Example 6 and ethyl vinyl ether (100 μl, 0.96 mmol) in dichloromethane (5 ml) is added a very small amount of paratoluenesulfonic acid while stirring under nitrogen atmosphere on an ice-water bath. After 10 minutes, to the mixture are added a saturated aqueous sodium hydrogencarbonate solution (15 ml) and n-hexane/ether (1:1) solution (20 ml) and the organic layer is separated. The aqueous layer is then extracted with n-hexane/ether (1:1) solution (20 ml) for several times. The organic layers are combined and dried over anhydrous sodium sulfate and the solvent is removed by distillation under reduced pressure. The resulting residue is purified by silca gel column chromatography (n-hexane/ ethyl acetate=20:1) to give 15-chloro-2-(1-ethoxyethoxy)-3-(1-methylethyl)-6,10,14-trimethyl -3,5,9,13-pentadecatetraenenitrile (207 mg, 85%).

Aufarbeitung

  1. additionis added a very small amount of paratoluenesulfonic acid
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is then extracted with n-hexane/ether (1:1) solution (20 ml) for several times
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent is removed by distillation under reduced pressure
  6. customThe resulting residue is purified by silca gel column chromatography (n-hexane/ ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-8184aa31f9c249b5af0c51bf4285fb30
Quelldatensatz
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05292911

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