반응 #1536

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N-t-butyl-3-(chloroacetyl)-2-thiophenesulfonamide

N-t-butyl-3-chloroacetyl-2-thiophenesulfonamide

acetic acid

sodium cyanoborohydride

→

title compound

수율 84.0%

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

수율 84.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타subjected to a vacuum evaporator
2. 2
   기타to remove the solvent
3. 3
   workup.ADDITIONTo the residue was added 10 ml of water
4. 4
   추출the resulting solution was extracted with methylene chloride
5. 5
   건조The extract was dried over anhydrous magnesium sulfate
6. 6
   여과filtered
7. 7
   workup.ADDITIONTo the filtrate were added acetic anhydride, pyridine and N,N-dimethylaminopyridine
8. 8
   workup.STIRRINGthe mixture was stirred at normal temperature for 24 hours
9. 9
   세척washed with 5% aqueous hydrochloric acid solution
10. 10
    기타The organic layer was separated
11. 11
    건조dried over anhydrous magnesium sulfate
12. 12
    여과filtered
13. 13
    농축The filtrate was concentrated

실험 절차

1.5 g (0.005 mole) of N-t-butyl-3-(chloroacetyl)-2-thiophenesulfonamide synthesized in Example 6 was dissolved in the combined solution of 1 ml of acetic acid and 10 ml of tetrahydrofuran and then 0.31 g (0.005 mole) of sodium cyanoborohydride was added slowly thereto. The reaction solution was stirred at normal temperature for 30 minutes and then subjected to a vacuum evaporator to remove the solvent. To the residue was added 10 ml of water and then the resulting solution was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and filtered. To the filtrate were added acetic anhydride, pyridine and N,N-dimethylaminopyridine and the mixture was stirred at normal temperature for 24 hours and then washed with 5% aqueous hydrochloric acid solution. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and the residue was subjected to column chromatography on silica gel to obtain 5 g (Yield: 84%) of the title compound. 1H NMR(CDCl3, δ): 1.3(s, 9H), 2.15(s, 3H), 3.57-3.9(m, 2H), 5.23(s, 1H), 6.5(m, 1H), 7.13(d, 1H), 7.5 (d, 1H)

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