Imidazole → HCID 58932261, compound

HRID 854205Notes

Reaction equation

HRID 854205 reaction equation
[C:1]([O:4][CH:5]1[CH:6]([CH3:38])[CH2:7][CH2:8][CH:9]([OH:37])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:36])=[CH:20]/[CH:21]=[CH:22]/[C:23]([OH:35])([CH3:34])[CH2:24][CH:25]2[O:33][CH:26]2[CH:27]([CH3:32])[CH:28]([OH:31])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2].N1[CH:43]=[CH:42]N=C1.[CH2:44]([Si:46](Cl)([CH2:50][CH3:51])[CH:47]([CH3:49])[CH3:48])[CH3:45]>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:4][CH:5]1[CH:6]([CH3:38])[CH2:7][CH2:8][CH:9]([O:37][Si:46]([CH2:42][CH3:43])([CH2:44][CH3:45])[CH:47]([CH3:49])[CH3:48])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:36])=[CH:20]/[CH:21]=[CH:22]/[C:23]([OH:35])([CH3:34])[CH2:24][CH:25]2[O:33][CH:26]2[CH:27]([CH3:32])[CH:28]([O:31][Si:46]([CH2:50][CH3:51])([CH2:44][CH3:45])[CH:47]([CH3:49])[CH3:48])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 4486980ChlorodiethylisopropylsilaneHCID 11964536HCID 11964536, compound

Product 1

HCID 58932261HCID 58932261, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (8E,12E,14E)-7-acetoxy-3,16,21-trihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (177 mg, 0.33 mmol) and imidazole (450 mg, 6.61 mmol) in methylene chloride (6 mL) was cooled to 5° C. A solution of diethylisopropylsilyl chloride (272 mg, 1.65 mmol) in methylene chloride (1.5 mL) was added dropwise to the reaction mixture, and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was diluted with ethyl acetate, and then the organic layer was washed with water. The resulting organic layer was washed with brine dried over 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 100 μm; ethyl acetate-hexane, 1:19->1:9->1:6->1:4) to obtain the title compound (242.9 mg, 93%) as a colorless oil.

Workup

  1. washthe organic layer was washed with water
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 100 μm; ethyl acetate-hexane, 1:19->1:9->1:6->1:4)

Sources & evidence

ORD record
ord-ffb24acb99354fe88f5c02601186fffe
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

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