Water → HCID 22123598, compound

HRID 1859331Notes

Reaction equation

HRID 1859331 reaction equation
COC[O:4][C:5]1[CH:47]=[CH:46][C:8]2[CH:9]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][S:35][CH2:36][CH2:37][CH2:38][C:39]([F:45])([F:44])[C:40]([F:43])([F:42])[F:41])[CH:24]=3)[CH:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19]COC)=[CH:15][CH:14]=3)[CH2:11][O:12][C:7]=2[CH:6]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>CO>[OH:4][C:5]1[CH:47]=[CH:46][C:8]2[CH:9]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][S:35][CH2:36][CH2:37][CH2:38][C:39]([F:45])([F:44])[C:40]([F:41])([F:42])[F:43])[CH:24]=3)[CH:10]([C:13]3[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=3)[CH2:11][O:12][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22123620HCID 22123620, compound

Product 1

HCID 22123598HCID 22123598, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-4-[3-(5-(4,4,5,5,5-pentafluoropentylthio)pentyloxy)phenyl]-2,3-dihydro-4H-benzopyran (290 mg, 0.4 mmol) and pyridinium p-toluenesulfonate (1.05 g, 4 mmol) were dissolved in methanol (6 ml) and then refluxed for 8 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 then concentrated under reduced pressure to remove the organic solvent. The concentrate was separated by column chromatography (n-hexane:ethyl acetate=1:1) to obtain 177mg (yield: 74%) of the title compound as a colorless oil.

Workup

  1. temperaturerefluxed for 8 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=1:1)

Sources & evidence

ORD record
ord-b497ea7920d34c6b8581b4755d36120a
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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