반응 #1973936

반응 방정식

1,3-butane diol

p-(trifluoromethyl)benzene-sulfonyl chloride

NaHCO3

1,3-butanediol

triethylamine

→

desired product

수율 67.9%

3-Hydroxybutyl 4-(trifluoromethyl)benzenesulfonate

수율 67.9%

용매

CH2Cl2

CH2Cl2

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   workup.WAITThe reaction was kept at −20° C. for an additional 3 hours
2. 2
   기타The reaction was quenched with water
3. 3
   세척washed with 10% aqueous HCl (5×30 mL), sat. NaHCO3 (3×20 mL), H2O (2×20 mL) and brine (1×20 mL)
4. 4
   건조The organic layer was dried over Na2SO4
5. 5
   기타the solvent was evaporated under reduced pressure
6. 6
   기타The product obtained
7. 7
   기타was purified by column chromatography
8. 8
   기타to get a white solid
9. 9
   기타Repeat synthesis
10. 10
    workup.STIRRINGThe solution was stirred at 0° C. for 2 h
11. 11
    workup.STIRRINGwas stirred at rt for 40 min
12. 12
    추출The organics were extracted with CH2Cl2 (50 mL)
13. 13
    세척washed with 1 M HCl (3×25 mL) and saturated aqueous NaCl (1×25 mL)
14. 14
    건조The organics were dried over Na2SO4
15. 15
    농축concentrated

실험 절차

A solution of 1,3-butanediol (2.00 g, 22.193 mmol) and triethylamine (2.695 g, 26.631 mmol) in 10 mL of methylene chloride was stirred at −20° C. under nitrogen. (4-trifluoromethyl)benzene sulfonyl chloride (5.429 g, 22.193 mmol) in 10 mL of methylene chloride was added drop wise to the solution, over 1 hr. The reaction was kept at −20° C. for an additional 3 hours and then stirred at room temperature for 24 hours. The reaction was quenched with water and then washed with 10% aqueous HCl (5×30 mL), sat. NaHCO3 (3×20 mL), H2O (2×20 mL) and brine (1×20 mL). The organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure. The product obtained was purified by column chromatography to get a white solid. (1.541 g, 23% yield). 1H NMR (400 MHz, CDCl3) δ1.19 (d, J=6.29, 3H, CH3), 1.66-1.76 (m, 1H, CH2), 1.80-1.91 (m, 1H, CH2), 3.93 (br. s, 1H, CH—OH), 4.14-4.23 (m, 1H, CH2O—SO2), 4.25-4.36 (m, 1H, CH2O—SO2), 7.81 (d, J=8.08, 2H, aromatic), 8.04 (d, J=8.71, 2H, aromatic). Repeat synthesis: To a solution of 1,3-butane diol (4.34 g, 48 mmol) and TEA (3.19 g, 31.5 mmol) in CH2Cl2 (20 mL) at 0° C. was added p-(trifluoromethyl)benzene-sulfonyl chloride (3.97 g, 16.2 mmol) dissolved in CH2Cl2 (20 mL). The solution was stirred at 0° C. for 2 h. Saturated aqueous NaHCO3 (15 mL) was added to the solution and mixture was stirred at rt for 40 min. The organics were extracted with CH2Cl2 (50 mL) and washed with 1 M HCl (3×25 mL) and saturated aqueous NaCl (1×25 mL). The organics were dried over Na2SO4 and concentrated to give the desired product (3.28 g, 65%). 1H NMR (400 MHz CDCl3) δ 8.02 (d, 2H, J=8.2 Hz), 7.80 (d, 2H, J=8.3), 4.29 (m, 1H), 4.17 (m, 1H), 3.91 (m, 1H), 1.83 (m, 1H), 1.70 (m, 1H), 1.17 (d, 3H, J=6.2 Hz); Anal. Calcd. For C11H13F3O4S: C, 44.29; H, 4.39. Found: C, 44.16; H, 4.17.

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