Reaction #1537

Reaction equation

N-t-butyl-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide

→

pure title compound

Yield 72.0%

3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide

Yield 72.0%

Solvents

trifluoroacetic acid

Conditions

Workup

1. 1
   Concentrationconcentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methylene chloride
3. 3
   Washthe solution was washed with aqueous sodium bicarbanate solution
4. 4
   OtherThe organic layer was separated
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe filtrate was then concentrated

Procedure

1.5 g (0.0044 mole) of N-t-butyl-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide synthesized in Example 7 was dissolved in 5 ml of trifluoroacetic acid. The reaction solution was stirred at normal temperature for 12 hours and then concentrated under reduced pressure. The residue was dissolved in methylene chloride and the solution was washed with aqueous sodium bicarbanate solution. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was then concentrated. The residue was subjected to column chromatograpy on silica gel to obtain 760 mg (Yield: 72%) of the pure title compound.

Source