Potassium Carbonate → HCID 86601408, compound

HRID 854198Notes

Reaction equation

HRID 854198 reaction equation
C([O:4][CH:5]1[CH:6]([CH3:53])[CH2:7][CH2:8][CH:9]([O:47][CH:48]([O:50][CH2:51][CH3:52])[CH3:49])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:46])=[CH:20]/[CH:21]=[CH:22]/[C:23]([O:40][CH:41]([O:43][CH2:44][CH3:45])[CH3:42])([CH3:39])[CH2:24][CH:25]2[O:38][CH:26]2[CH:27]([CH3:37])[CH:28]([O:31][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[CH2:51]([O:50][CH:48]([O:47][CH:9]1[CH2:8][CH2:7][CH:6]([CH3:53])[CH:5]([OH:4])[CH:17]=[CH:16][CH:15]([CH3:18])[CH:14](/[C:19](/[CH3:46])=[CH:20]/[CH:21]=[CH:22]/[C:23]([O:40][CH:41]([O:43][CH2:44][CH3:45])[CH3:42])([CH3:39])[CH2:24][CH:25]2[O:38][CH:26]2[CH:27]([CH3:37])[CH:28]([O:31][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])[CH2:29][CH3:30])[O:13][C:11](=[O:12])[CH2:10]1)[CH3:49])[CH3:52]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86601409HCID 86601409, compound

Product 1

HCID 86601408HCID 86601408, compoundYield 78.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(8E,12E,14E)-7-acetoxy-3,16,21-tris(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (186 mg) as the crude product was dissolved in methanol (2 mL). Potassium carbonate (75.0 mg, 543 μmol) was added to the reaction mixture, and the reaction mixture was stirred at room temperature for three hours. This reaction solution was diluted with ethyl acetate (50 mL), and the organic layer was washed with brine (10 mL) twice. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The resulting concentrate was purified by silica gel column chromatography (Merck Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=3:1->2:1) to obtain the title compound (131 mg, 185 μmol, 78.6%, 2 steps) as a colorless oil.

Workup

  1. washthe organic layer was washed with brine (10 mL) twice
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. concentrationThe resulting concentrate
  6. customwas purified by silica gel column chromatography (Merck Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=3:1->2:1)

Sources & evidence

ORD record
ord-0242ecc1733b4d3da783f3c5106c31b4
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

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