Reaktion #347380

ord-12c6fe906e2e4f26ba16d9e367215286

Reaktionsgleichung

C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O.O=C([O-])c1cccnc1
estrone nicotinate
CI
methyl iodide
CC(C)=O
acetone
→

Edukte

C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O.O=C([O-])c1cccnc1
estrone nicotinate
CI
methyl iodide
CC(C)=O
acetone

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe mixture was refluxed overnight
  2. 2
    FiltrationThe deep yellow precipitate was filtered
  3. 3
    Waschenwashed with acetone
  4. 4
    Sonstigedried

Vorschrift

To estrone nicotinate (0.5 g, 0.0013 mol) in acetone (20 ml) was added methyl iodide (1 ml, 0.016 mol) and the mixture was refluxed overnight. The deep yellow precipitate was filtered, washed with acetone, and dried. Yield 90% (0.6226 g); m.p. 245°-248° C. (dec.). NMR (d5 -DMSO) δ 9.8-9.7 (br s, 1H, C2 pyridinium proton), 9.4-9.0 (m, 2H, C4, C6 pyridinium protons), 8.4-8.0 (m, 1H, C5 pyridinium proton), 7.4-7.2 (m, 1H, C1 estrone proton), 7.1-6.9 (m, 2H, C2,4 estrone protons), 3.2-1.3 (estrone skeletal protons, 15), 1.0-0.9 (s, 3H, C18 estrone protons). IR (KBr) 1755-1740 (broad C=O stretching). Anal. calculated for C25H28NO3I: C, 58.03; H, 5.47; N, 2.71. Found: C, 58.16; H, 5.51; N, 2.67. The product has the formula: ##STR1466##

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05525727uspto-grants-1996_06