Water → HCID 21024001, compound

HRID 1446636Notes

Reaction equation

HRID 1446636 reaction equation
[C:1]1([CH3:11])C=CC(S([O-])(=O)=O)=CC=1.[NH+]1[CH:17]=[CH:16]C=CC=1.[C:18]([O:21][CH:22]1[C:23]([OH:55])([CH3:54])[CH2:24][CH2:25][CH:26]([OH:53])[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:56]([O:58][CH2:59][CH3:60])=[CH2:57].[C:61]([O:64][CH2:65][CH3:66])(=O)[CH3:62].[OH2:67]>ClCCl>[C:18]([O:21][CH:22]1[C:23]([O:55][CH:16]([O:67][CH2:1][CH3:11])[CH3:17])([CH3:54])[CH2:24][CH2:25][CH:26]([O:53][CH:61]([O:64][CH2:65][CH3:66])[CH3:62])[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:56]([O:58][CH2:59][CH3:60])[CH3:57])[CH2:46][CH3:47])[CH:32]([CH3:35])[CH:33]=[CH:34]1)=[O:29])(=[O:20])[CH3:19]

Participants

7

Reactant 5

HCID 962WaterHCID 8023Ethyl vinyl etherHCID 8857Ethyl AcetateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 9807215HCID 9807215, compound

Product 1

HCID 21024001HCID 21024001, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium p-toluenesulfonate (9 mg, 35.4 μmol) was added to a solution of (8E,12E,14E)-7-acetoxy-3,6,21-trihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (200 mg, 0.354 mmol) in dichloromethane (10 mL) and ethyl vinyl ether (521 mg, 7.08 mmol) at room temperature, followed by stirring at the same temperature overnight. Ethyl acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane=1:4, 1:3 and 1:1, successively) to obtain the title compound (250 mg, 94%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm

Sources & evidence

ORD record
ord-795b7faa86e64eaf9a374f07eae335d3
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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