反应详情

To a solution of 5.0 g (7.8×10-3 mol) of 2-(3-thienyl)-ethanol (Aldrich Chemical) in 10 ml of dry, freshly distilled pyridine was added 3.62 ml (1.2 equiv.) of methanesulfonyl chloride in 20 ml of pyridine at 5°-10° C. The addition was carried out gradually, over a period of about 15-20 min. The reaction mixture was stirred overnight at room temperature and was quenched by pouring into a separatory funnel containing water and ether. The layers were separated and the aqueous layer was extracted three times with ether. The combined organic extracts were extracted once with 10% hydrochloric acid, followed by water and drying over Na2SO4. Evaporation of the solvent afforded 5.3 g of a light brown oil (65% yield), and tlc (CHCl3) showed a single spot. Chromatographic purification on silica gel afforded a light yellow oil. Nmr (CDCl3, δ rel TMS) 2.9s, 3H; 3.1t, 2H; 4.4t, 2H; 7.0-7.4m, 3H. Ir (neat, ν cm-1) 3100w, 2930w, 2920w 1415w, 1355s, 1335s, 1245w, 1173s, 1080w, 1055w, 970s, 955s, 903m, 850m, 825w, 795s, 775s, 740w. MS, 206.0.

1. additionThe addition
2. customwas quenched
3. additionby pouring into a separatory funnel
4. additioncontaining water and ether
5. customThe layers were separated
6. extractionthe aqueous layer was extracted three times with ether
7. extractionThe combined organic extracts were extracted once with 10% hydrochloric acid
8. dry with materialdrying over Na2SO4
9. customEvaporation of the solvent