Sodium Bicarbonate → 2-(5,6-dihydro-2H-4-pyranyl)-1-benzenesulfonyl-5-methylthioindole

HRID 1432236Notes

Reaction equation

HRID 1432236 reaction equation
O[C:2]1([C:8]2[N:9]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:10]3[C:15]([CH:16]=2)=[CH:14][C:13]([S:17][CH3:18])=[CH:12][CH:11]=3)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1C=CC=CC=1>[O:5]1[CH2:6][CH2:7][C:2]([C:8]2[N:9]([S:19]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)(=[O:21])=[O:20])[C:10]3[C:15]([CH:16]=2)=[CH:14][C:13]([S:17][CH3:18])=[CH:12][CH:11]=3)=[CH:3][CH2:4]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 225044372-(4-hydroxytetrahydro-4H-4-pyranyl)-5-methylthio-1-benzenesulfonylindole

Product 1

HCID 225044022-(5,6-dihydro-2H-4-pyranyl)-1-benzenesulfonyl-5-methylthioindoleYield 90.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of the compound obtained in Example 14 (1) (39 mg) in benzene (10 ml), p-toluenesulfonic acid monohydrate (3.7 mg) was added and the mixture was heated under reflux for 1 hour. The reaction solution was then poured into a saturated aqueous sodium hydrogencarbonate solution, extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain 33.7 mg of the desired product as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-68550bf9cd8e46ef9148de404e3e0a0c
Source dataset
uspto-grants-2009_11
Patent number
US07612070B2

Reaction notes

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