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Ethyl bromoacetate → HCID 22034120, Verbindung

HRID 1792253
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1792253
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]([C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[CH3:25])[C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+].CC(C)([O-])C.[K+]>CS(C)=O.[NH4+].[Cl-]>[NH2:16][C:15]1[C:14]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])=[C:9]2[N:8]([C:2]=1[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:13]=[CH:12][CH:11]=[CH:10]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 220341262-(2-Pyridinyl)-2-(2,4,6-trimethylphenyl)ethanenitrileHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 22034120HCID 22034120, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 25517Ammonium ChlorideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Slowly add dropwise ethyl bromoacetate (23 mL; 0.21 mol) over a 3-hour period to a mixture of 2-(2-pyridinyl)-2-(2,4,6-trimethylphenyl)-ethanenitrile (22.3 g; 0.094 mol) and potassium carbonate (78 g; 0.57 mol) suspended in DMSO (100 mL). Stir the mixture for 1 day, pour into an aqueous NH4Cl solution (ca. 1 L), and extract with 3×200 mL of Et2O. Wash the combined extracts with saturated brine, dry over Na2SO4, filter, and concentrate in vacuo. Dissolve the residue in THF (200 mL), cool to 0° C., and add slowly in portions potassium t-butoxide (12 g; 0.11 mol) over a 10-minute period. After 30 minutes at 0° C., dilute the mixture with aqueous NH4Cl and extract with 2×150 mL of 50% Et2O in hexane. Wash the combined extracts with saturated brine, dry over Na2SO4, filter, concentrate in vacuo, and purify by column chromatography on silica gel (eluent: 5 to 10% EtOAc in hexane) to obtain the title compound as an oil: 1H NMR (400 MHz, CDCl3) δ 1.47 (t, 3H), 2.06 (s, 6H), 2.35 (s, 3H), 4.46 (br q, 2H), 6.6 (br t, 1H), 6.75 (d, 1H), 6.9 (br t, 1H), 7.00 (s, 2H), 9.4 (1H).

Aufarbeitung

  1. extractionextract with 3×200 mL of Et2O
  2. washWash the combined extracts with saturated brine
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. dissolutionDissolve the residue in THF (200 mL)
  7. waitAfter 30 minutes at 0° C.
  8. extractionextract with 2×150 mL of 50% Et2O in hexane
  9. washWash the combined extracts with saturated brine
  10. dry with materialdry over Na2SO4
  11. filtrationfilter
  12. concentrationconcentrate in vacuo
  13. custompurify by column chromatography on silica gel (eluent: 5 to 10% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-950f94b2156b4e3ba6cbaf232186d86d
Quelldatensatz
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07074929B2

Notizen zur Reaktion

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