Water → HCID 54296428, compound

HRID 1741977Notes

Reaction equation

HRID 1741977 reaction equation
[CH2:1]=[C:2]1[CH:7]2[O:8]C(C)(C)[O:10][CH:6]2[CH:5]([O:13][Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:4][C:3]1=[CH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33].C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(OCC)C>C(O)C>[CH2:1]=[C:2]1[CH:7]([OH:8])[CH:6]([OH:10])[CH:5]([O:13][Si:14]([C:27]([CH3:30])([CH3:28])[CH3:29])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:4][C:3]1=[CH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 54364816HCID 54364816, compound

Product 1

HCID 54296428HCID 54296428, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl (2-methylene-3,4-(dimethylmethylenedioxy)-5-(tert-butyldiphenylsilyloxy)cyclohexylidene)acetate (0.506 g) was dissolved in 10 ml of ethanol, and a catalytic amount of p-toluenesulfonic acid was added, followed by stirring the mixture at room temperature for 5 hours. Water 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 give 0.405 g of ethyl (2-methylene-3,4-dihydroxy-5-(tert-butyldiphenylsilyloxy)cyclohexylidene)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-14bf24e469a14fa3aeb6c728667302cf
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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