Acetic Acid → HCID 86610521, compound

HRID 495188Notes

Reaction equation

HRID 495188 reaction equation
C([O:4][C:5]1[C:6]([I:30])=[C:7]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:8]([C:15](=[O:24])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[C:9]([O:11]CC=C)[CH:10]=1)C=C.[Se](=O)=O.C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCOCC1>[OH:4][C:5]1[C:6]([I:30])=[C:7]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:8]([C:15](=[O:24])[C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[C:9]([OH:11])[CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24007Selenium DioxideHCID 516892Sodium BicarbonateHCID 86610522HCID 86610522, compound

Product 1

HCID 86610521HCID 86610521, compoundYield 8.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

Methyl 3,5-diallyloxy-2-iodo-6-(4-methoxybenzoyl)phenylacetate (80 mg, 0.15 mmol) obtained in Example 15, Step 2 was dissolved in 1,4-dioxane (1.0 mL), and selenium dioxide (36 mg, 0.34 mmol) and acetic acid (0.028 mL; 0.46 mmol) were added thereto, followed by stirring at 75° C. for half a day. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by preparative thin layer chromatography (chloroform/methanol=9/1) to obtain Compound 15 (1.2 mg, 8.2%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by preparative thin layer chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-e549d3adee25461fb574be7d1e1b6d18
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

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