Synthesis method of 4-(chlorosulfonyl)-1-butyl pivalate
A technology of butyl valerate and chlorosulfonyl, which is applied in the field of medicinal chemistry and achieves the effects of wide application prospects, easy industrialization, and high synthesis yield
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Embodiment 1
[0034] A kind of synthetic method of efficient 4-(chlorosulfonyl)-1-butyl pivalate comprises the following steps:
[0035] (1) 4-chloro-1-butanol (500g, 4.6mol) and organic base triethylamine (559g, 5.5mol) were dissolved in CH 2 Cl 2 (5 L), then the reaction apparatus was cooled to 0 °C. PivCl (618 g, 5.1 mol) was added dropwise over 4 hours. The mixture was stirred at 25 °C for 6 h. The reaction mixture was washed with water (5 L), 1M aqueous HCl (5 L) and brine (5 L), washed with Na 2 SO 4 dry. The solvent was removed under reduced pressure, and the crude product was further distilled under reduced pressure to obtain anhydrous oily 4-chloro-1-butyl pivalate (765g, yield: 86.2%, pressure: 5mmHg column, distillation temperature: 70~72°C) .
[0036] (2) 4-Chloro-1-butyl pivalate (500g, 2.6mol) and thiourea (198g, 2.6mol) were dissolved in ethanol (5L), and the mixture was heated to 90°C under reflux for 10h. The solvent was removed under reduced pressure and the residu...
Embodiment 2
[0039] A kind of synthetic method of efficient 4-(chlorosulfonyl)-1-butyl pivalate comprises the following steps:
[0040] (1) 4-chloro-1-butanol (500g, 4.6mol) and organic base diisopropylethylamine (637g, 5.5mol) were dissolved in CH 2 Cl 2 (5 L), then the reaction apparatus was cooled to 0 °C. PivCl (618 g, 5.1 mol) was added dropwise over 4 hours. The mixture was stirred at 25 °C for 6 h. The reaction mixture was washed with water (5 L), 1M aqueous HCl (5 L) and brine (5 L), washed with Na 2 SO 4 dry. The solvent was removed under reduced pressure, and the crude product was further distilled under reduced pressure to obtain anhydrous oily 4-chloro-1-butyl pivalate (736g, yield: 82.9%, pressure: 5mmHg column, distillation temperature: 70~72°C) .
[0041](2) Dissolve 4-chloro-1-butyl pivalate (500 g, 2.6 mol) and thiourea (217 g, 2.9 mol) in ethanol (5 L), then heat the mixture to 90° C. for 10 h under reflux. The solvent was removed under reduced pressure and the re...
Embodiment 3
[0044] A kind of synthetic method of efficient 4-(chlorosulfonyl)-1-butyl pivalate comprises the following steps:
[0045] (1) 4-chloro-1-butanol (500g, 4.6mol) and organic base 4-dimethylaminopyridine (765g, 5.3mol) were dissolved in CH 2 Cl 2 (5 L), then the reaction apparatus was cooled to 0 °C. PivCl (618 g, 5.1 mol) was added dropwise over 4 hours. The mixture was stirred at 25 °C for 6 h. The reaction mixture was washed with water (5 L), 1M aqueous HCl (5 L) and brine (5 L), washed with Na 2 SO 4 dry. The solvent was removed under reduced pressure, and the crude product was further distilled under reduced pressure to obtain anhydrous oily 4-chloro-1-butyl pivalate (728g, yield: 82.0%, pressure: 5mmHg column, distillation temperature: 70~72°C) .
[0046] (2) Dissolve 4-chloro-1-butyl pivalate (500 g, 2.6 mol) and thiourea (238 g, 3.1 mol) in ethanol (5 L), and then heat the mixture to 90° C. for 10 h under reflux. The solvent was removed under reduced pressure and...
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