反応 #1863305

反応方程式

(phenylthio)methyl 2-ethoxyacetate

sulfuryl chloride

cyclohexene

sulfuryl chloride

→

oil

収率 97.7%

chloromethyl 2-ethoxyacetate

収率 97.7%

溶媒

CH2Cl2

CH2Cl2

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   温度The reaction was again cooled to 0° C.
2. 2
   温度The reaction was then warmed to 30° C.
3. 3
   workup.STIRRINGstirred for 1 hour
4. 4
   温度cooled back to 0° C
5. 5
   workup.STIRRINGThe reaction was stirred at room temperature for 90 min
6. 6
   workup.WAITstored at −20° C. overnight
7. 7
   workup.DISTILLATIONpurified by vacuum distillation

実験手順

To a solution of (phenylthio)methyl 2-ethoxyacetate (17.28 g, 76 mmol) in CH2Cl2 (200 mL) at 0° C. was added a solution of sulfuryl chloride (7.36 mL, 92 mmol) in CH2Cl2 (50 mL) over a period of 15 min, and the reaction was stirred at room temperature for 90 min. The reaction was again cooled to 0° C. and treated with a second portion of sulfuryl chloride (7.36 mL, 92 mmol) in CH2Cl2 (50 mL) over a period of 15 min. The reaction was then warmed to 30° C., stirred for 1 hour, and then cooled back to 0° C. A solution of cyclohexene (24.5 mL, 242 mmol) in CH2Cl2 (50 mL) was added over a period of 10 min, during which gas evolution was observed. The reaction was stirred at room temperature for 90 min, stored at −20° C. overnight, and purified by vacuum distillation to give the target compound as a slightly yellow oil (11.33 g, 97%): by 58° C. at 6.8 mm Hg; 1H NMR (400 MHz, CDCl3) δ 5.77 (s, 2H), 4.16 (s, 2H), 3.62 (q, J=7.0 Hz, 2H), 1.27 (t, J=7.0 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 168.81, 68.59, 67.77, 67.48, 14.96.

出典