Water → HCID 15481762, compound

HRID 1859295Notes

Reaction equation

HRID 1859295 reaction equation
COC[O:4][C:5]1[CH:45]=[CH:44][C:8]2[CH:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][S:33][CH2:34][CH2:35][CH2:36][C:37]([F:43])([F:42])[C:38]([F:41])([F:40])[F:39])[C:10]([C:14]3[CH:19]=[CH:18][C:17]([O:20]COC)=[CH:16][CH:15]=3)([CH3:13])[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:45]=[CH:44][C:8]2[CH:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][S:33][CH2:34][CH2:35][CH2:36][C:37]([F:43])([F:42])[C:38]([F:39])([F:40])[F:41])[C:10]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)([CH3:13])[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 15481761HCID 15481761, compound

Product 1

HCID 15481762HCID 15481762, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3RS,4RS)-7-Methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylthio)nonyl]-2,3-dihydro-4H-benzopyran (100 mg, 0.15 mmol) and pyridinium p-toluenesulfonate (380 mg, 1.5 mmol) were dissolved in methanol (5 ml) and refluxed for 4 hours. The reaction solution was cooled to room temperature and, after adding water, extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography (n-hexane:ethyl acetate=4:1) to obtain 57 mg (yield: 66%) of the title compound as a colorless oil.

Workup

  1. temperaturerefluxed for 4 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracted organic layer was dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5dc3b4841cda4ad3b54a231c19c09194
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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