1,3-Butanediol → HCID 89723352, compound

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.

1. waitThe reaction was kept at −20° C. for an additional 3 hours
2. customThe reaction was quenched with water
3. washwashed with 10% aqueous HCl (5×30 mL), sat. NaHCO3 (3×20 mL), H2O (2×20 mL) and brine (1×20 mL)
4. dry with materialThe organic layer was dried over Na2SO4
5. customthe solvent was evaporated under reduced pressure
6. customThe product obtained
7. customwas purified by column chromatography
8. customto get a white solid
9. customRepeat synthesis
10. stirringThe solution was stirred at 0° C. for 2 h
11. stirringwas stirred at rt for 40 min
12. extractionThe organics were extracted with CH2Cl2 (50 mL)
13. washwashed with 1 M HCl (3×25 mL) and saturated aqueous NaCl (1×25 mL)
14. dry with materialThe organics were dried over Na2SO4
15. concentrationconcentrated

ORD record

ord-16240466215d413eafdc7cf42574bf69

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501382B1