Water → HCID 22123608, compound

HRID 1859304Notes

Reaction equation

HRID 1859304 reaction equation
O[C:2]1([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][S:38][CH2:39][CH2:40][CH2:41][C:42]([F:48])([F:47])[C:43]([F:46])([F:45])[F:44])=[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.C1(C)C=CC(S([O-])(=O)=O)=CC=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:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][S:38][CH2:39][CH2:40][CH2:41][C:42]([F:48])([F:47])[C:43]([F:44])([F:45])[F:46])=[CH:30][CH:31]=3)=[C:3]([C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[CH2:4][O:5][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22123595HCID 22123595, compound

Product 1

HCID 22123608HCID 22123608, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]4-[4-(5-(4,4,5,5,5-pentafluoropentylthio)pentyloxy)phenyl]-2,3-dihydro-4H-benzopyran (220 mg, 0.3 mmol) and pyridinium p-toluenesulfonate (789 mg, 3 mmol) were dissolved in methanol (8 mg) and then refluxed for 8 hours. The reaction solution was cooled to room temperature and, after adding water, extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure to remove the organic solvent. The concentrate was subjected to column chromatography (n-hexane:ethyl acetate=1:1) to obtain 142 mg (yield, 78%) of the title compound as a colorless oil.

Workup

  1. temperaturerefluxed for 8 hours
  2. extractionextracted 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. customto obtain

Sources & evidence

ORD record
ord-305a2e49b5784d49a73578ec2b61eb58
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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