Methyl iodide → Methyl corosolate

HRID 1367637Notes

Reaction equation

HRID 1367637 reaction equation
[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

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6918774Corosolic acid

Product 1

HCID 14109751Methyl corosolateYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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)−.

Workup

  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

Sources & evidence

ORD record
ord-f911532d017e4c1ba7e594675be67879
Source dataset
uspto-grants-2011_02
Patent number
US07893263B2

Reaction notes

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