Réaction #476533

Équation de réaction

Compound ( 1 )

O-(1-Chloroethyl) S-Methyl Thiocarbonate

isobutyric acid

isobutyric acid

diisopropylethylamine

→

title compound ( 6 )

Rendement 97.0%

O-(1-Isobutanoyloxyethyl) S-Methyl Thiocarbonate

Rendement 97.0%

Solvants

ether

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water (2×10 mL), saturated bicarbonate solution (2×10 mL) and brine (10 mL)
2. 2
   Séchagedried over anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated in vacuo

Mode opératoire

Compound (1) (308 mg, 2 mmol) was dissolved in isobutyric acid (264 mg, 3 mmol). This mixture was slowly added to a pre-mixed solution of isobutyric acid (264 mg, 3 mmol) and diisopropylethylamine (387 mg, 3 mmol) and the reaction mixture heated to 55° C. for 16 h, diluted with ether (50 mL), washed with water (2×10 mL), saturated bicarbonate solution (2×10 mL) and brine (10 mL), then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound (6) as colorless liquid (400 mg, 97%). The product was further purified by vacuum distillation (135° C./20 Torr). 1H NMR (CDCl3, 400 MHz): δ 1.17 (d, J=6.8 Hz, 6H), 1.49 (d, J=5.6 Hz, 3H), 2.33 (s, 3H), 2.54 (m, 1H), 6.91 (q, J=5.2 Hz, 1H).

Source