Water → HCID 22123617, compound

HRID 1859334Notes

Reaction equation

HRID 1859334 reaction equation
O[C:2]1([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:28][CH:27]=2)[C:7]2[CH:8]=[CH:9][C:10]([O:12]COC)=[CH:11][C:6]=2[O:5][CH2:4][CH:3]1[C:16]1[CH:21]=[CH:20][C:19]([O:22]COC)=[CH:18][CH:17]=1.[NH+]1C=CC=CC=1.O>CO>[OH:12][C:10]1[CH:9]=[CH:8][C:7]2[C:2]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]4[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]4)=[CH:28][CH:27]=3)=[C:3]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH2:4][O:5][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4989215PyridiniumHCID 22123586HCID 22123586, compound

Product 1

HCID 22123617HCID 22123617, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-4-[4-(piperidinoethyloxy)phenyl]-2,3-dihydro-4H-benzopyran (83 mg, 0.14 mmol) and pyridinium p-toulenesulfonate (214 mg, 1.4 mmol) were dissolved in methanol (6 ml) and then refluxed for 12 hours. The reaction solution was cooled to room temperature and, after adding water, extracted with ethyl acetate. The organic layer thus separated was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure to remove the organic solvent. The residue was separated by column chromatography (n-hexane:ethyl acetate=1:4) to obtain 23 mg (yield: 37%) of the title compound as a foam.

Workup

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

Sources & evidence

ORD record
ord-3968e6eb9b424b6fb4e51327917542f5
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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