Water → HCID 57278514, compound

HRID 729116Notes

Reaction equation

HRID 729116 reaction equation
[CH3:1][C:2](=[CH:7][CH2:8][CH2:9][C:10]([CH3:28])=[CH:11][CH2:12][CH2:13][CH:14]=[C:15]([CH3:27])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH2:3][CH2:4][CH2:5][OH:6].O.[CH:30](OCC)=[CH2:31]>C([O-])(=O)C.C([O-])(=O)C.[Hg+2]>[CH:30]([O:6][CH2:5][CH2:4][CH2:3][C:2]([CH3:1])=[CH:7][CH2:8][CH2:9][C:10]([CH3:28])=[CH:11][CH2:12][CH:13]=[CH:14][CH:15]([CH3:27])[CH2:16][CH2:17][CH:18]=[C:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])=[CH2:31]

Participants

5

Reactant 3

HCID 962WaterHCID 8023Ethyl vinyl etherHCID 54420527HCID 54420527, compound

Product 1

HCID 57278514HCID 57278514, compound

Reagents, catalysts & solvents 1

HCID 15337Mercuric acetateCatalyst

Procedure

Mercury diacetate (0.33 g, 1.03 mmol) was added to a solution of 4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaen-1-ol (2.00 g, 5.17 mmol) in 50 ml of ethyl vinyl ether and the reaction refluxed overnight. The reaction was poured into 350 ml of water and extracted with ether. Theether extracts were washed with brine and dried over magnesium sulfate. Removal of the ether in vacuo gave the crude material which was purified by flash chromatography usin9 95/5 (hexane/ethyl acetate), to give 1.69 g of 4,8,13,17,21-pentamethyl-4,8,11,16,20-docosapentaen-1-ol vinyl ether.

Workup

  1. temperaturethe reaction refluxed overnight
  2. extractionextracted with ether
  3. washTheether extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the ether in vacuo
  6. customgave the crude material which
  7. customwas purified by flash chromatography usin9 95/5 (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-903b97cadc9247f589f78f9741592720
Source dataset
uspto-grants-1991_09
Patent number
US05051534

Reaction notes

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