Reaktion #1928060

Reaktionsgleichung

Methyl 4-formylbenzoate

N-hexyl-6-acetyl 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one

Intermediate 6a

N-hexyl-6-acetyl 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one

→

title compound

Ausbeute 33.0%

4-[3-(1-Hexyl-4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-3-oxo-propenyl]-benzoic acid

Ausbeute 33.0%

Lösungsmittel

NaOH

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe reaction mixture was extracted with ethyl acetate (3×10 mL)
2. 2
   WaschenThe combined organic layer was washed with brine (1×10 mL)
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenconcentrated at reduced pressure
5. 5
   SonstigePurification by flash chormatography (50:49:1 hexane/ethyl acetate/acetic acid)

Vorschrift

Methyl 4-formylbenzoate (22 mg, 13.4 mmol) was added to a solution of N-hexyl-6-acetyl 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (Intermediate 6a, 40 mg, 13.3 mmol) in 2 mL of 1 N NaOH and 4 mL of methanol. After stirring at room temperature for 18 h, the reaction mixture was extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chormatography (50:49:1 hexane/ethyl acetate/acetic acid) gave the title compound as a light yellow solid (18.9 mg, 33% yield).

Quelle