Sodium Iodide → HCID 23116450, compound

HRID 495197Notes

Reaction equation

HRID 495197 reaction equation
[CH2:1]([O:4][C:5]1[C:6]([CH2:31][CH3:32])=[C:7]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[C:8]([C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([OH:24])[CH:17]=2)=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:42][CH2:43][O:44][CH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][O:46]1>CN(C)C=O.O>[CH2:1]([O:4][C:5]1[C:6]([CH2:31][CH3:32])=[C:7]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[C:8]([C:15](=[O:25])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:42][CH2:43][O:44][CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][O:46]3)[CH:17]=2)=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 86610527HCID 86610527, compound

Product 1

HCID 23116450HCID 23116450, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 3,5-diallyloxy-2-ethyl-6-(3-hydroxy-4-methoxybenzoyl)phenylacetate (330 mg, 0.75 mmol) obtained in Example 82, Step 1 was dissolved in N,N-dimethylformamide (10 mL), and potassium carbonate (550 mg, 4.0 mmol), sodium iodide (100 mg, 0.67 mmol) and 2-(2-bromoethoxy)tetrahydro-2H-pyran (0.6 mL, 4.0 mmol) were added thereto with stirring at room temperature. The reaction mixture was stirred at 80° C. for 3 hours and cooled to room temperature, and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with 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=1/4-1/1) to obtain methyl 3,5-diallyloxy-2-ethyl-6-[4-methoxy-3-(2-tetrahydro-2H-pyran-2-yloxyethoxy)benzoyl]phenylacetate.

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for 3 hours
  2. temperaturecooled to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/1)

Sources & evidence

ORD record
ord-c5ad452d95ff4763abcee26b0b63e7fe
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

Loading…