Methanesulfonic Acid → 2-Dipropylamino-8-methylsulfinyl-1,2,3,4-tetrahydronaphthalene
Reaction equation
[CH3:1][S:2]([OH:5])(=O)=O.[CH2:6]([N:9]([CH2:22][CH2:23][CH3:24])[CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[C:13](SC)[CH:14]=[CH:15][CH:16]=2)[CH2:11]1)[CH2:7][CH3:8].I([O-])(=O)(=O)=O.[Na+].[NH4+].[OH-]>O>[CH2:22]([N:9]([CH2:6][CH2:7][CH3:8])[CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[C:13]([S:2]([CH3:1])=[O:5])[CH:14]=[CH:15][CH:16]=2)[CH2:11]1)[CH2:23][CH3:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of water (60 mL) which contains methanesulfonic acid (0.16 mL, 2.33 mMol) was added 2-dipropylamino-8-methylthio-1,2,3,4-tetrahydronaphthalene (630 mg, 2.33 mMol). To this solution was added a solution of sodium metaperiodate (550 mg, 2.57 mMol) in water (10 mL), and the reaction mixture was stirred for two days at room temperature. The reaction mixture was made basic (NH4OH) and extracted with dichloromethane. The organic extracts were combined, dried (Na2SO4) and concentrated in vacuo to give the crude title compound as a light yellow oil. Purification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH) gave the desired product (580 mg, 85%) as a colorless oil. The fumarate salt was formed. Recrystallization (ethanol/diethyl ether) gave a colorless, crystalline solid which was found to be extremely hygroscopic. Drying in a vacuum dessicator (60° C., 18 hours) gave a colorless glass (260 mg, m.p.=63° C.).
Workup
- extractionextracted with dichloromethane
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customto give the crude title compound as a light yellow oil
- customPurification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH)
Sources & evidence
- ORD record
- ord-8c88f92d668b4906af92c5f60200bc8a
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05096908
Reaction notes
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