Methanol → HCID 86610525, compound

HRID 495196Notes

Reaction equation

HRID 495196 reaction equation
[CH2:1]([O:4][C:5]1[C:6]([CH2:30][CH3:31])=[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][CH:19]=[C:18](SC)[CH:17]=2)=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3].O[O:33][S:34]([O-:36])=O.[K+].[CH3:38]O>O>[CH2:1]([O:4][C:5]1[C:6]([CH2:30][CH3:31])=[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][CH:19]=[C:20]([S:34]([CH3:38])(=[O:36])=[O:33])[CH:21]=2)=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 86610526HCID 86610526, compound

Product 1

HCID 86610525HCID 86610525, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Methyl 3,5-diallyloxy-2-ethyl-6-(3-methylsulfanylbenzoyl)phenylacetate (550 mg, 1.3 mmol) obtained in Example 94, Step 1 was dissolved in a mixed solvent of methanol (12 mL) and water (6 mL), and Oxone (trademark; 1.9 g, 3.1 mmol) was slowly added thereto with stirring under ice-cooling. The reaction mixture was stirred at room temperature for 3 hours, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed successively with a saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to obtain methyl 3,5-diallyloxy-2-ethyl-6-(3-methanesulfonylbenzoyl)phenylacetate (550 mg, 93%).

Workup

  1. additionwas slowly added
  2. temperaturecooling
  3. stirringThe reaction mixture was stirred at room temperature for 3 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed successively with a saturated aqueous solution of sodium thiosulfate
  6. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-894644783ec94e378e702b5f5b831220
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

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