反応 #958990

反応方程式

Tetrahydrothiapyran-4-ol

triethylamine

Methacryloyl chloride

→

tetrahydro-2H-thiopyran-4-yl methacrylate

収率 64.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他The reaction
2. 2
   温度then was warmed slowly to room temperature
3. 3
   洗浄the reaction was washed with DIW (20 mL), 1 M NaOH (2×20 mL), DIW (20 mL), 1 M HCl (20 mL), DIW (20 mL) and brine (20 mL)
4. 4
   乾燥The organic layer then was dried over sodium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated by rotary evaporation
7. 7
   その他dried in vacuo

実験手順

Tetrahydrothiapyran-4-ol (4.81 g, 40.7 mmol) and triethylamine (6.2 mL, 44.5 mmol) were dissolved in anhydrous dichloromethane (60 mL) and cooled to 0° C. Methacryloyl chloride (4.0 mL, 45.0 mmol) then was added slowly, dropwise. The reaction then was warmed slowly to room temperature. After stirring overnight, the reaction was washed with DIW (20 mL), 1 M NaOH (2×20 mL), DIW (20 mL), 1 M HCl (20 mL), DIW (20 mL) and brine (20 mL). The organic layer then was dried over sodium sulfate, filtered, and then concentrated by rotary evaporation and dried in vacuo to afford tetrahydro-2H-thiopyran-4-yl methacrylate as a pale yellow liquid (4.85 g, 61%). 1H NMR (600 MHz, CDCl3, ppm) δ 6.07 (s, 1H), 5.52 (s, 1H), 4.88 (m, 1H), 2.77 (m, 2H), 2.55 (m, 2H), 2.07 (m, 2H), 1.90 (m, 5H). 13C NMR (150 MHz, CDCl3, ppm) δ 166.29, 166.23 (minor), 136.55, 13.70 (minor), 125.40 (multiplet: 126.58, 126.31, 125.72, 125.28, 125.07, 124.65, 124.19), 70.86, 69.86 (minor), 32.33 (multiplet: 32.59, 32.44, 32.21, 32.04), 25.71 (multiplet: 26.66, 26.19, 25.71, 25.44, 24.95), 18.26 (multiplet: 18.43, 18.09).

出典