Hydrochloric Acid → Ethyl 2-(4-benzyloxyphenyl)cyanoacetate

HRID 398026

Reaktionsgleichung

Reaktionsgleichung von HRID 398026
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][C:14]#[N:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Na+].[C:22](=O)([O:26]CC)[O:23][CH2:24][CH3:25].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]([C:14]#[N:15])[C:22]([O:23][CH2:24][CH3:25])=[O:26])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 5228044-BenzyloxyphenylacetonitrileHCID 2723922Sodium ethoxide

Produkt 1

HCID 23001570Ethyl 2-(4-benzyloxyphenyl)cyanoacetateAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The 4-benzyloxybenzyl cyanide from step (450a)(3.2 g, 14.33 mmol), sodium ethoxide (1.07 g, 15.7 mmol), and diethyl carbonate (2.23 g, 18.9 mmol) were combined in toluene (100 mL), heated to reflux for 3 h, cooled to rt, and partioned between ethyl acetate and 1 N HCl. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The crude was purified by chromatography on silica gel eluting hexane:ethyl acetate (80:20, v:v) to give ethyl 2-(4-benzyloxyphenyl)cyanoacetate (4.2 g, 99%) as an oil. MS (M+NH4)+=313.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by chromatography on silica gel
  7. washeluting hexane:ethyl acetate (80:20, v:v)

Quellen und Nachweise

ORD-Eintrag
ord-94741de82d734d9693cabe305f6d8d9d
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610731B2

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