Potassium Carbonate → HCID 86602606, compound

HRID 1366324Notes

Reaction equation

HRID 1366324 reaction equation
C([O:4][CH:5]1[C:6]([O:54][CH:55]([O:57][CH2:58][CH3:59])[CH3:56])([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][C:6]([O:54][CH:55]([O:57][CH2:58][CH3:59])[CH3:56])([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 86602607HCID 86602607, compound

Product 1

HCID 86602606HCID 86602606, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (8E,12E,14E)-7-acetoxy-3,6,16,21-tetrakis(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (145 mg, 0.17 mmol) in methanol (2.5 mL) was added potassium carbonate (95 mg, 0.69 mmol) at room temperature, followed by stirring at the same temperature for two hours and 30 minutes. The reaction mixture was diluted with ethyl acetate and then washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtrated and evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 100 μm; ethyl acetate:hexane=40:60) to give the title compound (128 mg, 93%) as a colorless oil. ESI-MS m/z 821 (M+Na)+.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltrated
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 100 μm; ethyl acetate:hexane=40:60)

Sources & evidence

ORD record
ord-fc1cfe1d5c944033a09f28f867e4b696
Source dataset
uspto-grants-2011_02
Patent number
US07893068B2

Reaction notes

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