반응 #53846

반응 방정식

3-bromo-1-propanol

2,6-di-tert-butylpyridine

trifluoromethansulfonic anhydride

trans-N-(4-Hydroxymethyl-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide

2,6-di-tert-butylpyridine

→

trans-N-[4-(3-Bromo-propoxymethyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide

수율 64.0%

용매

CH2Cl2

CH2Cl2

nitromethane

반응 조건

후처리

1. 1
   기타the violet solution was evaporated
2. 2
   workup.DISSOLUTIONdissolved in 1 ml nitromethane
3. 3
   추출extracted with aqueous 10% KHSO4/EtOAc (3×)
4. 4
   세척The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl
5. 5
   건조dried over Na2SO4
6. 6
   기타evaporated
7. 7
   기타Purification by flash-chromatography on silica gel (hexane/EtOAc 9:1)

실험 절차

[following a procedure of Belostotskii, Anatoly M.; Hassner, Alfred. Synthetic methods. 41. Etherification of hydroxysteroids via triflates. Tetrahedron Lett. (1994), 35(28), 5075-6.]. A solution of 0.175 ml (2 mmol) 3-bromo-1-propanol and 0.48 ml 2,6-di-tert-butylpyridine in 1 ml CH2Cl2 was treated at 0° C. with a solution of 0.35 ml (2.1 mmol) trifluoromethansulfonic anhydride in 0.5 ml CH2Cl2. After 2.5 h at 0° C., the violet solution was evaporated, dissolved in 1 ml nitromethane and treated with a solution of 0.375 g (1 mmol) trans-N-(4-Hydroxymethyl-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide and 0.45 ml (2 mmol) 2,6-di-tert-butylpyridine in 3 ml nitromethane (during 3 min). The reaction was heated (60° C.) for 3.5 h and then extracted with aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried over Na2SO4 and evaporated. Purification by flash-chromatography on silica gel (hexane/EtOAc 9:1) yielded 0.3 g (64%) of trans-N-[4-(3-Bromo-propoxymethyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide, MS: 452 (M−F, 1Br).

출처