Water → 4-[3-(5-iodopentyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran

HRID 1859330Notes

Reaction equation

HRID 1859330 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]2[C:19]3[CH:20]=[CH:21][C:22]([O:24][CH2:25][O:26][CH3:27])=[CH:23][C:18]=3[O:17][CH2:16][CH:15]2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:30][CH:29]=2)[CH:11]=[CH:12][CH:13]=1.[I-:38].[Na+].O>C(C(C)=O)C>[I:38][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]2[C:19]3[CH:20]=[CH:21][C:22]([O:24][CH2:25][O:26][CH3:27])=[CH:23][C:18]=3[O:17][CH2:16][CH:15]2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:30][CH:29]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 221236054-[3-(5-chloropentyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran

Product 1

HCID 221235944-[3-(5-iodopentyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyranYield 94.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-[3-(5-Chloropentyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran (283 mg, 0.5 mmol) and sodium iodide (24 mg, 1.6 mmol) were dissolved in methyl ethyl ketone (5 ml) and then refluxed for 12 hours. The reaction mixture was cooled to room temperature and then water was added thereto. The reaction solution was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to remove the organic solvent. The concentrate was separated by column chromatography (n-hexane:ethyl acetate=8:1) to obtain 293 mg (yield: 94%) of the title compound as a yellow oil.

Workup

  1. temperaturerefluxed for 12 hours
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto remove the organic solvent
  7. customThe concentrate was separated by column chromatography (n-hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-b4c26c419f2c49cc8c45a7962d33d67e
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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