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

HRID 1030215Notes

Reaction equation

HRID 1030215 reaction equation
O[C@H:2]1[C@H:7]([N:8]2[CH2:12][CH2:11][CH2:10][S:9]2(=[O:14])=[O:13])[C:6]2[CH:15]=[C:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:17]=[CH:18][C:5]=2[O:4][C:3]1([CH3:24])[CH3:23].C(OC(=O)C)(=O)C.O>N1C=CC=CC=1>[O:14]=[S:9]1(=[O:13])[CH2:10][CH2:11][CH2:12][N:8]1[C:7]1[C:6]2[CH:15]=[C:16]([S:19]([CH3:22])(=[O:20])=[O:21])[CH:17]=[CH:18][C:5]=2[O:4][C:3]([CH3:23])([CH3:24])[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 67792343trans-3,4-dihydro-3-hydroxy-4-(1,1-dioxoisothiazolidin-2-yl)-6-mesyl-2,2-dimethyl-2H-1-benzopyran

Product 1

HCID 157348204-(1,1-dioxoisothiazolidin-2-yl)-6-mesyl-2,2-dimethyl-2H-1-benzopyranYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of trans-3,4-dihydro-3-hydroxy-4-(1,1-dioxoisothiazolidin-2-yl)-6-mesyl-2,2-dimethyl-2H-1-benzopyran (0.32 g) in pyridine (10 ml) was treated with acetic anhydride (5 ml), and the mixture was stood at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and brine, and then dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure gave the crude product, which was purified by recrystallization from ethyl acetate to give 4-(1,1-dioxoisothiazolidin-2-yl)-6-mesyl-2,2-dimethyl-2H-1-benzopyran (0.14 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with 1N hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and brine, and then dried over anhydrous magnesium sulfate
  4. customRemoval of the solvent under reduced pressure
  5. customgave the crude product, which
  6. customwas purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-12da0770602f48eab66cac55d9960738
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

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