Ethyl vinyl ether → HCID 21024015, compound

HRID 1446631Notes

Reaction equation

HRID 1446631 reaction equation
[CH:1]([O:3][CH2:4][CH3:5])=[CH2:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:23]([O:26][CH:27]1[CH:39]=[CH:38][CH:37]([CH3:40])[CH:36]([C:41]([CH3:63])=[CH:42][CH:43]=[CH:44][CH:45]([CH3:62])[CH2:46][CH:47]2[O:61][CH:48]2[CH:49]([CH3:60])[CH:50]([O:53][C:54](=[O:59])[CH2:55][O:56][CH2:57][CH3:58])[CH2:51][CH3:52])[O:35][C:33](=[O:34])[CH2:32][CH:31]([O:64][Si:65]([C:68]([CH3:71])([CH3:70])[CH3:69])([CH3:67])[CH3:66])[CH2:30][CH2:29][C:28]1([OH:73])[CH3:72])(=[O:25])[CH3:24]>ClCCl.C(OCC)(=O)C>[C:23]([O:26][CH:27]1[C:28]([O:73][CH:1]([O:3][CH2:4][CH3:5])[CH3:2])([CH3:72])[CH2:29][CH2:30][CH:31]([O:64][Si:65]([C:68]([CH3:69])([CH3:70])[CH3:71])([CH3:66])[CH3:67])[CH2:32][C:33]([O:35][CH:36](/[C:41](/[CH3:63])=[CH:42]/[CH:43]=[CH:44]/[CH:45]([CH3:62])[CH2:46][CH:47]2[O:61][CH:48]2[CH:49]([CH3:60])[CH:50]([O:53][C:54](=[O:59])[CH2:55][O:56][CH2:57][CH3:58])[CH2:51][CH3:52])[CH:37]([CH3:40])[CH:38]=[CH:39]1)=[O:34])(=[O:25])[CH3:24]

Participants

6

Reactant 3

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 73734140HCID 73734140, compound

Product 1

HCID 21024015HCID 21024015, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl vinyl ether (82 mg, 1.1 mmol) and pyridinium p-toluenesulfonate (9.2 mg, 0.036 mmol) were added to a solution of 7-acetoxy-3-t-butyldimethylsiloxy-21-ethoxyacetoxy-6-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (27 mg, 0.036 mmol) in dichloromethane (1.5 mL) at room temperature. The mixture was stirred at room temperature for 17 hours. The reaction solution was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The resulting crude product was purified by silica gel column chromatography (Kanto silica gel 60N, spherical, neutral, 40 to 100 μm, eluate; hexane:ethyl acetate=80:20) to obtain the title compound (16 mg, 54%) as a colorless oil.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated
  4. customThe resulting crude product was purified by silica gel column chromatography (Kanto silica gel 60N, spherical, neutral, 40 to 100 μm, eluate; hexane:ethyl acetate=80:20)

Sources & evidence

ORD record
ord-533a4d8ce2a1489294611fc2cdc811f2
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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