Iodoethane → N-{3-ethoxybicyclo[1.1.1]pentan-1-yl}acetamide

HRID 62607

Reaktionsgleichung

Reaktionsgleichung von HRID 62607
[OH:1][C:2]12[CH2:6][C:4]([NH:7][C:8](=[O:10])[CH3:9])([CH2:5]1)[CH2:3]2.[H-].[Na+].I[CH2:14][CH3:15]>C1COCC1>[CH2:14]([O:1][C:2]12[CH2:6][C:4]([NH:7][C:8](=[O:10])[CH3:9])([CH2:5]1)[CH2:3]2)[CH3:15]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 86287953N-{3-hydroxybicyclo[1.1.1]pentan-1-yl}acetamide

Produkt 1

HCID 86287954N-{3-ethoxybicyclo[1.1.1]pentan-1-yl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a anhydrous THF (5 mL) solution of N-(3-hydroxybicyclo[1.1.1]pentan-1-yl)acetamide (1) (1 mmol) is added NaH (60% dispersion in mineral oil, 3 mmol) portionwise at 0° C. After addition, the mixture is stirred until the evolution of gas stops. Iodoethane (1 mmol) is then added by syringe slowly. The reaction is monitored by LCMS and TLC. After consumption of starting material, the reaction mixture is quenched by adding water (3 mL) and extracted with ethyl acetate (3×). The organic layers are combined, dried (magnesium sulfate), filtered, and concentrated. The crude residue is subjected to flash chromatography (silica gel, EtOAc/hexanes) to afford N-(3-ethoxybicyclo[1.1.1]pentan-1-yl)acetamide (2).

Aufarbeitung

  1. additionAfter addition
  2. customAfter consumption of starting material
  3. customthe reaction mixture is quenched
  4. additionby adding water (3 mL)
  5. extractionextracted with ethyl acetate (3×)
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7041294fee3745909557675e4ea95d88
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447025B2

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