Chloroform → HCID 18516753, compound

HRID 1369905

Reaction equation

HRID 1369905 reaction equation
[CH3:1][C:2]1[CH2:3][S:4]([CH2:7][CH:8]=1)(=[O:6])=[O:5].[OH-].[Na+].[CH:11](Cl)(Cl)Cl>>[CH3:11][C:2]1[CH:1]=[CH:8][CH2:7][S:4](=[O:5])(=[O:6])[CH:3]=1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 70941Thiophene, 2,5-dihydro-3-methyl-, 1,1-dioxide2×

Product 1

HCID 18516753HCID 18516753, compound

Procedure

5-Methyl-2H-thiopyran-1,1-dioxide is prepared in three steps from 3-methyl-3-sulfolene using the method of Gaoni, J. Org. Chem., 46 (1981) 4502. Thus, 3-methyl-3-sulfolene is first reacted with chloroform and aqueous sodium hydroxide in the presence of a quaternary ammonium salt to give the dichlorocarbene adduct. Partial dehalogenation with lithium aluminum hydride in tetrahydrofuran gives the chlorocyclopropane. Finally, base-catalyzed ring expansion with lithium diisopropylamide gives the desired thiopyran dioxide compound (see Scheme 1, above).

Sources & evidence

ORD record
ord-34896faa3465482585a60501d151772d
Source dataset
uspto-grants-2003_06
Patent number
US06579957B2

Linked notes

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