Ethyl vinyl ether → HCID 86602615, compound

HRID 1987547Notes

Reaction equation

HRID 1987547 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]/[C:23]([OH:42])([CH3:41])[CH2:24][CH:25]2[O:40][CH:26]2[CH:27]([CH3:39])[CH:28]([O:31][Si:32]([CH2:37][CH3:38])([CH2:35][CH3:36])[CH2:33][CH3:34])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2].[CH2:54]([O:56][CH:57]=[CH2:58])[CH3:55]>ClCCl.C(OCC)(=O)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:1]([O:4][CH2:5][CH3:17])[CH3:2])([CH3:52])[CH2:7][CH2:8][CH:9]([O:44][Si:45]([CH2:46][CH3:47])([CH2:48][CH3:49])[CH2:50][CH3:51])[CH2:10][C:11]([O:13][CH:14](/[C:19](/[CH3:43])=[CH:20]/[CH:21]=[CH:22]/[C:23]([O:42][CH:57]([O:56][CH2:54][CH3:55])[CH3:58])([CH3:41])[CH2:24][CH:25]2[O:40][CH:26]2[CH:27]([CH3:39])[CH:28]([O:31][Si:32]([CH2:33][CH3:34])([CH2:35][CH3:36])[CH2:37][CH3:38])[CH2:29][CH3:30])[CH:15]([CH3:18])[CH:16]=[CH:17]1)=[O:12])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 8023Ethyl vinyl etherHCID 86602614HCID 86602614, compound

Product 1

HCID 86602615HCID 86602615, compoundYield 132.8%

Reagents, catalysts & solvents 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Compound 129 (8E,12E,14E)-7-acetoxy-6,16-dihydroxy-6,10,12,16,20-pentamethyl-3,21-bis(triethylsiloxy)-18,19-epoxytricosa-8,12,14-trien-11-olide (320 mg, 0.41 mmol) obtained in Example 129 and ethylvinyl ether (589 mg, 8 mmol) in dichloromethane (6 mL) was added a solution of pyridinium p-toluenesulfonate (5 mg, 20 μmol) in dichloromethane (1 mL) at room temperature, and the reaction mixture was stirred at the same temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water and a saturated aqueous solution of sodium bicarbonate, 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, 1:9 to 1:7) to give the title compound (252 mg, 67%) as a colorless oil.

Workup

  1. washwashed with water
  2. dry with materiala saturated aqueous solution of sodium bicarbonate, dried 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, 1:9 to 1:7)

Sources & evidence

ORD record
ord-6624af5ba94a47a7ac444bce425a9e4f
Source dataset
uspto-grants-2009_06
Patent number
US07550503B2

Reaction notes

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