2-Butene, 1-bromo-3-methyl- → 2-Methoxy-3-(3-methyl-2-butenyl)-2,4,4-trimethyloxazolidine

HRID 894413

Reaktionsgleichung

Reaktionsgleichung von HRID 894413
[CH3:1][C:2]1[O:3][CH2:4][C:5]([CH3:8])([CH3:7])[N:6]=1.[CH3:9][C:10]([CH3:14])=[CH:11][CH2:12]Br.[CH3:15][O-:16].[Na+]>C(Cl)Cl>[CH3:15][O:16][C:2]1([CH3:1])[N:6]([CH2:12][CH:11]=[C:10]([CH3:14])[CH3:9])[C:5]([CH3:8])([CH3:7])[CH2:4][O:3]1

Komponenten

5

Edukt 3

HCID 700922-Butene, 1-bromo-3-methyl-HCID 744964,5-Dihydro-2,4,4-trimethyloxazoleHCID 10942334Sodium Methoxide

Produkt 1

HCID 204742602-Methoxy-3-(3-methyl-2-butenyl)-2,4,4-trimethyloxazolidineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

226 g (2 mols) of 2,4,4-trimethyloxazoline were dropped at room temperature to 298 g (2 mols) 3-methyl-2-butenyl bromide in 400 ml absolute methylenchloride and were stirred for 12 hours at 20° C. After cooling to 0° C. 400 ml (2 mols) of a 30% solution of sodium methylate were added and the mixture was stirred for a further hour at room temperature. The solution was filtered and after removing off the solvent the residue was distilled. 368 g (1.72 mols, 86%) of 2-methoxy-3-(3-methyl-2-butenyl)-2,4,4-trimethyloxazolidine of boiling point 70°-76° C./0.05 mm Hg were obtained. NMR (CDCL3): α1.1 (s, 3H); 1.2 (s, 3H); 1.4 (s, 3H); 1.6-1.7 (bs, 6H); 3.2 (s, 3H); 3.25 (d, J=6.5 Hz, 2H); 3.65 (s, 2H); 5.25 (t, J=6.5 Hz, 1H).

Aufarbeitung

  1. temperatureAfter cooling to 0° C
  2. stirringthe mixture was stirred for a further hour at room temperature
  3. filtrationThe solution was filtered
  4. customafter removing off the solvent the residue
  5. distillationwas distilled

Quellen und Nachweise

ORD-Eintrag
ord-6cd0ad6f5b514f64a5ccdac555488191
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04283544

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