HCID 10036812, Verbindung → 3-(1,3-Dioxolan-2-yl)-2-(2-methoxymethoxy-5-methylbenzoyl)pyridine

HRID 862085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 862085
Br[C:2]1[C:7]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.CCCCCC.C([Li])CCC.[CH3:24][O:25][CH2:26][O:27][C:28]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][C:29]=1[C:30](OCOC)=[O:31]>C1COCC1>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:7]1[C:2]([C:30](=[O:31])[C:29]2[CH:36]=[C:37]([CH3:40])[CH:38]=[CH:39][C:28]=2[O:27][CH2:26][O:25][CH3:24])=[N:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 10036812HCID 10036812, VerbindungHCID 19701585Methoxymethyl 2-methoxymethoxy-5-methylbenzoateHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 197015733-(1,3-Dioxolan-2-yl)-2-(2-methoxymethoxy-5-methylbenzoyl)pyridineAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-bromo-3-(1,3-dioxolan-2-yl)pyridine (3.50 g) in THF (50 ml) was added, at -78° C. under argon atmosphere, a 1.6M n-butyl lithium hexane solution (10.5 ml), which was stirred for 20 minutes. This reaction mixture was added, at the same temperature under argon atmosphere, to a solution of methoxymethyl 2-methoxymethoxy-5-methylbenzoate (3.66 g) in THF (50 ml). The mixture was stirred for 40 minutes, then for further one hour while warming up to room temperature. The reaction mixture was poured into a saturated aqueous saline solution, followed by extraction with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution, dried (anhydrous sodium sulfate) and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to give 3-(1,3-dioxolan-2-yl)-2-(2-methoxymethoxy-5-methylbenzoyl)pyridine (2.06 g) (Compound E-14). The physical properties and spectrum data are shown in Table 16 and Table 19.

Aufarbeitung

  1. additionThe reaction mixture was poured into a saturated aqueous saline solution
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract solution was washed with a saturated aqueous saline solution
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated
  6. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-88e5e0125cad43eebe318c5630f29be9
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716971

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