Réaction #476536

Équation de réaction

compound ( 4 )

O-(1-Chloroethyl) S-Phenyl Thiocarbonate

isobutyric acid

triethylamine

sodium iodide

→

title compound ( 9 )

Rendement 97.0%

O-(1-Isobutanoyloxyethyl) S-Phenyl Thiocarbonate

Rendement 97.0%

Solvants

diethyl ether

Conditions de réaction

Traitement

1. 1
   Lavagewashed successively with water (3×100 mL), saturated aqueous sodium bicarbonate (2×100 mL) and 0.1 M aqueous potassium bisulfate (2×100 mL)
2. 2
   AutreThe organic phase was separated
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo

Mode opératoire

A mixture of compound (4) (10 g, 46 mmol), isobutyric acid (30 mL), triethylamine (30 mL) and sodium iodide (2 g) was stirred and heated in an oil bath at 50° C. for 3 days. The reaction mixture was diluted with diethyl ether (200 mL) and washed successively with water (3×100 mL), saturated aqueous sodium bicarbonate (2×100 mL) and 0.1 M aqueous potassium bisulfate (2×100 mL). The organic phase was separated, then dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the title compound (9) as a pale yellow liquid (12 g, 97%). 1H NMR (CDCl3, 400 MHz): δ 1.2 (d, 6H), 1.5 (d, 3H), 2.55 (m, 1H), 6.95 (q, 1H), 7.4-7.5 (m, 5H).

Source