Methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetate → 3,3-Dimethyl-1-[2-benzylperhydropyridazinyl]pentane-1,2-dione

HRID 2228455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2228455
[O:1]=[C:2]([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][N:8]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5]C)=O.[CH3:20][C:21]([Mg]Cl)([CH3:24])[CH2:22][CH3:23]>C1COCC1>[CH3:20][C:21]([CH3:24])([CH2:22][CH3:23])[C:3](=[O:5])[C:2]([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][N:8]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:1]

Komponenten

4

Edukt 2

HCID 18470067Methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetateHCID 178446075HCID 178446075, Verbindung

Produkt 1

HCID 184700773,3-Dimethyl-1-[2-benzylperhydropyridazinyl]pentane-1,2-dioneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetate (9.0 g, 29.4 mmol) in 30 ml dry THF was cooled to −78° C. and treated with 35 ml of 1.0 M solution of 1,1-dimethylpropylmagnesium chloride in THF. After stirring the resulting homogeneous mixture at for 5 hours, the mixture was poured into saturated. ammonium chloride (150 ml) and extracted into ethyl acetate. The organic layer was washed with water, dried and concentrated. The crude material was purified by silica gel column, eluting with 10% ethyl acetate in hexane, to obtain 7.0 g product (69% yield) as clear oil. 1H NMR (CDCl3, 400 MHz): δ 0.76 (t, 3H, J=7.0); 1.06 (s, 6H); 1.69 (m, 6H); 2.80 (m, 1H); 3.15 (m, 1H), 4.03 (m, 1H); 4.13 (m, 1H), 5.18 (m, 2H), 7.36 (m, 5H).

Aufarbeitung

  1. additionthe mixture was poured into saturated
  2. extractionammonium chloride (150 ml) and extracted into ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel column
  7. washeluting with 10% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-2c028398ff534b05803c03d511217a33
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06417189B1

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