Methyl iodide → Methyl corosolate

HRID 1367637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367637
[CH3:1][C@H:2]1[C@H:29]([CH3:30])[C@@H:28]2[C@@:5]([C:32]([OH:34])=[O:33])([CH2:6][CH2:7][C@@:8]3([CH3:31])[C@:13]4([CH3:27])[CH2:14][CH2:15][C@H:16]5[C:21]([CH3:23])([CH3:22])[C@@H:20]([OH:24])[C@H:19]([OH:25])[CH2:18][C@:17]5([CH3:26])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1.IC.[C:37](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C@H:2]1[C@H:29]([CH3:30])[C@@H:28]2[C@@:5]([C:32]([O:34][CH3:37])=[O:33])([CH2:6][CH2:7][C@@:8]3([CH3:31])[C@:13]4([CH3:27])[CH2:14][CH2:15][C@H:16]5[C:21]([CH3:23])([CH3:22])[C@@H:20]([OH:24])[C@H:19]([OH:25])[CH2:18][C@:17]5([CH3:26])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6918774Corosolic acid

Produkt 1

HCID 14109751Methyl corosolateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of corosolic acid (2.0 g, 4.34 mmol), iodomethane (1 mL, 16 mmol), potassium carbonate (4.5 g, 32.6 mmol) and acetone (60 mL) was stirred at rt for 16 h. After completion of the reaction, the solids were filtered off and the solvent was evaporated under reduced pressure. The residue was chromatographed over silica gel column using chloroform-methanol (10%) as eluent to furnish methyl corosolate (1.7 g, 83%), which was recrystallised from chloroform-hexane, m.p. 208-210° C.; IR (KBr): 3432, 2946, 2872, 1728, 1455, 1230, 1197, 1049 cm−1; 1H NMR (400 MHz, CDCl3) δ 0.75 (3H, s, CH3), 0.83 (3H, s, CH3), 0.85 (3H, d, J=6.5 Hz, CH3), 0.94 (3H, d, J=5.7 Hz, CH3), 0.99 (3H, s, CH3), 1.03 (3H, s, CH3), 1.08 (3H, s, CH3), 2.23 (1H, d, J=11.0 Hz, H-18), 3.0 (1H, d, J=8.4 Hz, H-3), 3.60 (3H, s, —COOCH3), 3.62-3.71 (1H, m, H-2), 5.25 (1H, t, J=3.4 Hz, H-12); LCMS (negative ion mode): m/z 485 (M−H)−.

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe solids were filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was chromatographed over silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-f911532d017e4c1ba7e594675be67879
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893263B2

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