Water → trans-3,4-dihydro-3-hydroxy-4-(1,1-dioxoisothiazolidin-2-yl)-6-mesyl-2,2-dimethyl-2H-1-benzopyran

HRID 1030214Notes

Reaction equation

HRID 1030214 reaction equation
[O:1]1[CH:7]2[CH:2]1[C:3]([CH3:17])([CH3:16])[O:4][C:5]1[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:6]=12.[Na].[S:19]1(=[O:25])(=[O:24])[CH2:23][CH2:22][CH2:21][NH:20]1.O>CS(C)=O>[OH:1][C@H:2]1[C@H:7]([N:20]2[CH2:21][CH2:22][CH2:23][S:19]2(=[O:25])=[O:24])[C:6]2[CH:8]=[C:9]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=[CH:11][C:5]=2[O:4][C:3]1([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6421571,3-PropanesultamHCID 5360545SodiumHCID 142103893,4-dihydro-3,4-epoxy-6-mesyl-2,2-dimethyl-2H-1-benzopyran

Product 1

HCID 67792343trans-3,4-dihydro-3-hydroxy-4-(1,1-dioxoisothiazolidin-2-yl)-6-mesyl-2,2-dimethyl-2H-1-benzopyranYield 21.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3,4-dihydro-3,4-epoxy-6-mesyl-2,2-dimethyl-2H-1-benzopyran (1.5 g) in dimethyl sulfoxide (30 ml) was added sodium salt of isothiazolidine 1,1-dioxide (1.7 g). The mixture was stirred at room temperature overnight. Water was carefully added to the reaction mixture and the whole was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (50 g) with a mixture of chloroform and methanol (50:1) as eluents to give trans-3,4-dihydro-3-hydroxy-4-(1,1-dioxoisothiazolidin-2-yl)-6-mesyl-2,2-dimethyl-2H-1-benzopyran (0.47 g).

Workup

  1. extractionthe whole was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (50 g) with a mixture of chloroform and methanol (50:1) as eluents

Sources & evidence

ORD record
ord-3595fbf47c074a75882049127004830d
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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