Sodium Chloride → Ethyl (2E)-3-phenyl-2-butenoate

HRID 16647

Reaktionsgleichung

Reaktionsgleichung von HRID 16647
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[C:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)[CH3:18].[Cl-].[Na+]>O1CCCC1>[C:20]1(/[C:17](/[CH3:18])=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 7410AcetophenoneHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

Produkt 1

HCID 5354836Ethyl (2E)-3-phenyl-2-butenoateAusbeute 128,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 10 g (0.25 mol) of sodium hydride and tetrahydrofuran is heated to 50° C., followed by dropwise addition over 30 minutes of a solution of 48 ml (0.19 mol) of ethyl diethylphosphonoacetate in 80 ml of tetrahydrofuran. A solution of 28.4 g (0.24 mol) of acetophenone in 60 ml of tetrahydrofuran is added dropwise at 0° C. and the mixture is stirred for 16 hours at 25° C. 250 ml of saturated sodium chloride solution are added at 0° C. and the resulting mixture is extracted with ether. The organic phase is dried (Na2SO4) and the solvents are evaporated off under reduced pressure. The 46.6 g of product obtained are purified by flash chromatography (90/10 cyclohexane/diisopropyl ether) (29 g; 63%).

Aufarbeitung

  1. extractionthe resulting mixture is extracted with ether
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. customthe solvents are evaporated off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e57508df4c494718b30ab937cbf2203a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737176B2

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