Diethyl Ether → HCID 54269160, compound

HRID 1741976Notes

Reaction equation

HRID 1741976 reaction equation
[CH2:1]=[C:2]1[CH:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][CH:6]2[CH:5]([O:13]C(OCC)C)[CH2:4][C:3]1=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+].C(OCC)C>C(O)C>[CH2:1]=[C:2]1[CH:7]2[O:8][C:9]([CH3:12])([CH3:11])[O:10][CH:6]2[CH:5]([OH:13])[CH2:4][C:3]1=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 54238111HCID 54238111, compound

Product 1

HCID 54269160HCID 54269160, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl (2-methylene-3,4-(dimethylmethylenedioxy)-5-(1-ethoxyethoxy)cyclohexylidene)acetate was dissolved in 5 ml of ethanol, and a catalytic amount of pyridinium p-toluenesulfonate was added, followed by stirring at room temperature for 15 minutes. A sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and extraction was conducted with diethyl ether. The extract was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to afford 0.202 g of ethyl (2-methylene-3,4-(dimethylmethylenedioxy)-5-hydroxycyclohexylidene)acetate having the following property.

Workup

  1. washThe extract was washed with a saturated sodium chloride aqueous solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b9d7108aed414e3eb3087cd48eb50e5b
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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