Ethyl Acetate → HCID 86608518, compound

HRID 2104197Notes

Reaction equation

HRID 2104197 reaction equation
[C:1]([O:4][CH:5]1[C:6]([OH:53])([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:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:71]([O:74][CH2:75][CH3:76])(=O)[CH3:72]>C(Cl)Cl.C(OCC)=C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[C:1]([O:4][CH:5]1[C:6]([O:53][CH:71]([O:74][CH2:75][CH3:76])[CH3:72])([CH3:52])[CH2:7][CH2:8][CH:9]([O:44][Si:45]([CH2:48][CH3:49])([CH2:46][CH3:47])[CH2:50][CH3:51])[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:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86608516HCID 86608516, compound

Product 1

HCID 86608518HCID 86608518, compoundYield 85.1%

Reagents, catalysts & solvents 3

HCID 8023Ethyl vinyl etherCatalyst2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

(8E,12E,14E)-7-acetoxy-21-benzoyloxy-6-hydroxy-6,10,12,16,20-pentamethyl-3-triethylsiloxy-18,19-epoxytricosa-8,12,14-trien-11-olide (95.6 mg, 127 μmol) was dissolved in methylene chloride (2 mL). Ethyl vinyl ether (200 μL, 2.09 μmol) and pyridinium p-toluenesulfonate (3.2 mg, 12.7 μmol) were added to the solution at room temperature, and the reaction solution was stirred at the same temperature for 14.5 hours. Ethyl vinyl ether (200 μl, 2.09 μmol) and pyridinium p-toluenesulfonate (2.5 mg, 9.9 μmol) were further added to the reaction solution at room temperature, and the reaction solution was stirred at the same temperature for 7.5 hours. The reaction solution was diluted with ethyl acetate (30 mL), and the dilution was washed with 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) to obtain the title compound (89.1 mg, 108 μmol, 85.1%) as a colorless oil.

Workup

  1. stirringthe reaction solution was stirred at the same temperature for 7.5 hours
  2. washthe dilution was washed with purified water (6 mL) twice
  3. dry with materialThe resulting organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customThe concentrate was purified by silica gel column chromatography (MERCK Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0a5d4cee339b417782ec0ebdf68b48ce
Source dataset
uspto-grants-2009_08
Patent number
US07576204B2

Reaction notes

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