N-Methoxy-N,3-dimethylbenzamide → Cyclopropyl 3-methylphenyl ketone

HRID 1620990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620990
CON(C)[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1.[CH:14]1([Mg]Br)[CH2:16][CH2:15]1>C1COCC1>[CH:14]1([C:4]([C:5]2[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=2)=[O:12])[CH2:16][CH2:15]1

Komponenten

4

Edukt 2

HCID 11171317N-Methoxy-N,3-dimethylbenzamideHCID 178418630HCID 178418630, Verbindung

Produkt 1

HCID 21431776Cyclopropyl 3-methylphenyl ketoneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-methoxy-N,3-dimethylbenzamide (2.86 g, 16 mmol) in THF (50 mL) was added cyclopropylmagnesium bromide (2 N in THF, 40 mmol, 20 mL) dropwise at 0° C. After addition, the reaction mixture was stirred for 4 hours at room temperature and quenched with 30 mL of aqueous NH4Cl. The aqueous phase was separated and extracted with ethyl acetate (50 mL×2). The combined organic phase was washed with water (50 mL), brine (50 mL), dried over Na2SO4, filtered, and concentrated to give crude product as a yellow oil (2.56 g, 100%). LC-MS (M+H): m/z 161. 1H NMR (400 MHz, CDCl3): δ ppm 7.817 (s, 2H), 7.367-7.332 (m, 2H), 2.697-2.635 (m, 1H), 2.417 (s, 3H), 1.247-1.209 (m, 2H), 1.046-1.000 (m, 2H).

Aufarbeitung

  1. additionAfter addition
  2. customquenched with 30 mL of aqueous NH4Cl
  3. customThe aqueous phase was separated
  4. extractionextracted with ethyl acetate (50 mL×2)
  5. washThe combined organic phase was washed with water (50 mL), brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5d36a0af02f94b7a98a340aedc5d14eb
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772500B2

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