Potassium Carbonate → HCID 86601413, compound

HRID 854202Notes

Reaction equation

HRID 854202 reaction equation
C([O:4][CH:5]1[CH:6]([CH3:59])[CH2:7][CH2:8][CH:9]([O:51][Si:52]([CH2:57][CH3:58])([CH2:55][CH3:56])[CH2:53][CH3:54])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:50])=[CH:20]/[CH:21]=[CH:22]/[C:23]([CH3:49])([O:41][Si:42]([CH2:47][CH3:48])([CH2:45][CH3:46])[CH2:43][CH3:44])[CH2:24][CH:25]2[O:40][CH:26]2[CH:27]([CH3:39])[CH:28]([O:31][Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])[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>[OH:4][CH:5]1[CH:6]([CH3:59])[CH2:7][CH2:8][CH:9]([O:51][Si:52]([CH2:53][CH3:54])([CH2:57][CH3:58])[CH2:55][CH3:56])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:50])=[CH:20]/[CH:21]=[CH:22]/[C:23]([CH3:49])([O:41][Si:42]([CH2:47][CH3:48])([CH2:43][CH3:44])[CH2:45][CH3:46])[CH2:24][CH:25]2[O:40][CH:26]2[CH:27]([CH3:39])[CH:28]([O:31][Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86601412HCID 86601412, compound

Product 1

HCID 86601413HCID 86601413, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

(8E,12E,14E)-7-acetoxy-6,10,12,16,20-pentamethyl-3,16,21-tris(triethylsiloxy)-18,19-epoxytricosa-8,12,14-trien-11-olide (77 mg, 0.0875 mmol) was dissolved in methanol (2 mL). Potassium carbonate (36.5 mg, 0.262 mmol) and methanol (1 mL) were added to this methanolic solution, and the reaction mixture was stirred at room temperature for four hours. The reaction mixture was diluted with ethyl acetate, and then the organic layer was washed with brine. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:9->1:6->1:4->1:3) to obtain the title compound (38.6 mg, 50%) as a colorless oil.

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:9->1:6->1:4->1:3)

Sources & evidence

ORD record
ord-f64bfcb478094ae581c0cf117496ea9a
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

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