Acetic Acid → HCID 86608519, compound

HRID 2104198Notes

Reaction equation

HRID 2104198 reaction equation
C([O:4][CH:5]1[C:6]([O:53][CH:54]([O:56][CH2:57][CH3:58])[CH3:55])([CH3:52])[CH2:7][CH2:8][CH:9]([O:44][Si:45]([CH2:50][CH3:51])([CH2:48][CH3:49])[CH2:46][CH3:47])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:43])=[CH:20]/[CH:21]=[CH:22]/[CH:23]([CH3:42])[CH2:24][CH:25]2[O:41][CH:26]2[CH:27]([CH3:40])[CH:28]([O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=O)C.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CO>[C:32]([O:31][CH:28]([CH2:29][CH3:30])[CH:27]([CH3:40])[CH:26]1[O:41][CH:25]1[CH2:24][CH:23]([CH3:42])/[CH:22]=[CH:21]/[CH:20]=[C:19](\[CH3:43])/[CH:14]1[O:13][C:11](=[O:12])[CH2:10][CH:9]([O:44][Si:45]([CH2:48][CH3:49])([CH2:46][CH3:47])[CH2:50][CH3:51])[CH2:8][CH2:7][C:6]([O:53][CH:54]([O:56][CH2:57][CH3:58])[CH3:55])([CH3:52])[CH:5]([OH:4])[CH:17]=[CH:16][CH:15]1[CH3:18])(=[O:39])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 86608518HCID 86608518, compound

Product 1

HCID 86608519HCID 86608519, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(8E,12E,14E)-7-acetoxy-21-benzoyloxy-6-(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-3-triethylsiloxy-18,19-epoxytricosa-8,12,14-trien-11-olide (89.1 mg, 108 μmol) was dissolved in methanol (3 mL), and the solution was cooled to 0° C. Potassium carbonate (30.2 mg, 219 μmol) was added to the reaction solution. The reaction solution was warmed to room temperature, and stirred at the same temperature for 3.5 hours. Acetic acid (12.3 μL, 215 μmol) was added to the reaction solution, and then the solution was concentrated. The concentrate was suspended in ethyl acetate (30 mL), and the suspension was washed with saturated aqueous solution of sodium hydrogencarbonate (6 mL) twice, purified water (6 mL) twice, and brine (6 mL). The resulting organic layer was dried over sodium sulfate, and then filtered. The filtrate was concentrated. The concentrate was purified by silica gel column chromatography (MERCK Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=5:1→4:1) to obtain the title compound (60.9 mg, 77.6 μmol, 72.1%) as a colorless oil.

Workup

  1. temperatureThe reaction solution was warmed to room temperature
  2. concentrationthe solution was concentrated
  3. washthe suspension was washed with saturated aqueous solution of sodium hydrogencarbonate (6 mL) twice
  4. custompurified water (6 mL) twice
  5. dry with materialThe resulting organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customThe concentrate was purified by silica gel column chromatography (MERCK Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=5:1→4:1)

Sources & evidence

ORD record
ord-d00045949e8d4a26ad91b7f87155b837
Source dataset
uspto-grants-2009_08
Patent number
US07576204B2

Reaction notes

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