Réaction #1763154

Équation de réaction

tert-butyl thiol

1-chloroethyl chloroformate

N-Methylmorpholine

→

title compound ( 3 )

Rendement 89.0%

O-(1-Chloroethyl) S-tert-Butyl Thiocarbonate

Rendement 89.0%

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water (2×1 L), saturated bicarbonate solution (1 L) and brine (1 L)
2. 2
   Séchagedried over anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated in vacuo
5. 5
   workup.DISTILLATIONThe residue was purified by vacuum distillation (135° C./20 Torr)

Mode opératoire

A solution of tert-butyl thiol (180 g, 2 mol) and 1-chloroethyl chloroformate (284 g, 2 mol) in CH2Cl2 (1 L) was cooled to 0° C. in an ice-water bath. N-Methylmorpholine (212.1 g, 2.1 mol) was added dropwise over a period of 1 h and the reaction mixture was allowed to stir at room temperature for 16 h. The reaction mixture was diluted with excess CH2Cl2 (2 L), washed with water (2×1 L), saturated bicarbonate solution (1 L) and brine (1 L), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by vacuum distillation (135° C./20 Torr) to provide the title compound (3) as a colorless liquid (350 g, 89%). 1H NMR (CDCl3, 400 MHz): δ 1.50 (s, 9H), 1.79 (d, J=6 Hz, 3H), 6.57 (q, J=5.6 Hz, 1H).

Source