Sodium Carbonate → HCID 69766328, compound

HRID 498110Notes

Reaction equation

HRID 498110 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]2[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH:16]=[CH:15][CH2:14]2)=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH:13]2[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH:16]=[CH:15][CH2:14]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 69766068HCID 69766068, compound

Product 1

HCID 69766328HCID 69766328, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

0.17 g of 5-[2-(4-methoxymethoxyphenyl)ethyl]-2-cyclooctene-1-one prepared in Example 12 was dissolved in 10 ml of 50% aqueous solution of trifluoroacetic acid. The resulting solution was stirred at room temperature for forty minutes. The reaction solution was cooled in an ice bath, and to the solution was added slowly 30 ml of a saturated sodium carbonate aqueous solution. Then, the reaction solution was extracted with ether. The extract was washed with a saturated sodium bicarbonate aqueous solution six times, and dried over anhydrous sodium sulfate. The solvent was evaporated. The residue was purified on silica gel column, and the eluate with ethyl acetate-hexane (1:6) was collected, to afford 0.077 g of the title compound above as colorless liquid.

Workup

  1. temperatureThe reaction solution was cooled in an ice bath
  2. extractionThen, the reaction solution was extracted with ether
  3. washThe extract was washed with a saturated sodium bicarbonate aqueous solution six times
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customThe residue was purified on silica gel column
  7. customthe eluate with ethyl acetate-hexane (1:6) was collected

Sources & evidence

ORD record
ord-d3a1030a5a1548e0b4b836cac1ad1572
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

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