Iodoethane → N-(4-(2-ethylbutanoyl)phenyl)acetamide

HRID 538883

Reaktionsgleichung

Reaktionsgleichung von HRID 538883
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[Li+].[CH3:17][CH:18]([N-]C(C)C)C.C1COCC1.ICC>C1COCC1>[CH2:3]([CH:2]([CH2:17][CH3:18])[C:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:5])[CH3:4]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 4304236N-(4-Butyrylphenyl)acetamideHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)

Produkt 1

HCID 43160160N-(4-(2-ethylbutanoyl)phenyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of N-(4-butyrylphenyl)acetamide (3 g, 14.6 mmol) in THF (300 mL) was added 2.0 M LDA THF (18.3 mL) at −78° C. and then the reaction mixture was stirred for 1 h at −78° C. Iodoethane was added and stirred overnight at RT. The reaction mixture was quenched with sat. aq. NH4Cl and then extracted with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and then concentrated. The crude product was purified by preparative TLC using 50% ethyl acetate in hexane as eluent to afford N-(4-(2-ethylbutanoyl)phenyl)acetamide as white solid. MS (ES+): m/z 234.28 (MH+).

Aufarbeitung

  1. stirringstirred overnight at RT
  2. customThe reaction mixture was quenched with sat. aq. NH4Cl
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-fecdf382f0564c6ebddbfea5285b64fe
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865752B2

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