Ethyl vinyl ether → HCID 21024017, compound

HRID 1795674Notes

Reaction equation

HRID 1795674 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:21][CH:22]1[C:23]([OH:62])([CH3:61])[CH2:24][CH2:25][CH:26]([O:53][Si:54]([C:57]([CH3:60])([CH3:59])[CH3:58])([CH3:56])[CH3:55])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:52])=[CH:37]/[CH:38]=[CH:39]/[CH:40]([CH3:51])[CH2:41][CH:42]2[O:50][CH:43]2[CH:44]([CH3:49])[CH:45]([OH:48])[CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]1)=[O:29])(=[O:20])[CH3:19].[CH:63]([O:65][CH2:66][CH3:67])=[CH2:64].[C:68]([O:71][CH2:72][CH3:73])(=O)[CH3:69]>C(Cl)Cl>[C:18]([O:21][CH:22]1[C:23]([O:62][CH:68]([O:71][CH2:72][CH3:73])[CH3:69])([CH3:61])[CH2:24][CH2:25][CH:26]([O:53][Si:54]([C:57]([CH3:58])([CH3:60])[CH3:59])([CH3:56])[CH3:55])[CH2:27][C:28]([O:30][CH:31](/[C:36](/[CH3:52])=[CH:37]/[CH:38]=[CH:39]/[CH:40]([CH3:51])[CH2:41][CH:42]2[O:50][CH:43]2[CH:44]([CH3:49])[CH:45]([O:48][CH:63]([O:65][CH2:66][CH3:67])[CH3:64])[CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]1)=[O:29])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 8023Ethyl vinyl etherHCID 8857Ethyl AcetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21024018HCID 21024018, compound

Product 1

HCID 21024017HCID 21024017, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium p-toluenesulfonate (1.8 mg, 7 μmol) was added to a solution of (8E,12E,14E)-7-acetoxy-3-(t-butyldimethylsiloxy)-6,21-dihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (44 mg, 67 μmol) obtained in Example B10 and ethyl vinyl ether (98 mg, 1.35 mmol) in methylene chloride (3 mL), and the mixture was stirred at room temperature for 18 hours. The reaction solution was diluted with ethyl acetate, washed with distilled water and brine, dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm, ethyl acetate:hexane=1:4 to 1:2) to obtain the title compound (35 mg, 66%) as a colorless oil.

Workup

  1. washwashed with distilled water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm, ethyl acetate:hexane=1:4 to 1:2)

Sources & evidence

ORD record
ord-4c84ba239e85480abbb28e64f1d775f6
Source dataset
uspto-grants-2006_04
Patent number
US07026352B1

Reaction notes

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