Reaction #632030

Reaction equation

Compound ( 3 )

O-(1-Chloroethyl) S-Methyl Thiocarbonate

isobutyric acid

isobutyric acid

diisopropylethylamine

→

title compound ( 2 )

Yield 97.0%

O-(1-Isobutanoyloxyethyl) S-Methyl Thiocarbonate

Yield 97.0%

Solvents

ether

Conditions

Workup

1. 1
   Washwashed with water (4×5 L), saturated bicarbonate solution (2×5 L) and brine (5 L)
2. 2
   Dryingdried over anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated in vacuo

Procedure

Compound (3) (308 g, 2 mol) was dissolved in isobutyric acid (264 g, 3 mol). This mixture was slowly added to a pre-mixed solution of isobutyric acid (264 g, 3 mol) and diisopropylethylamine (387 g, 3 mol), and the reaction mixture heated to 55° C. for 16 h, diluted with ether (10 L), washed with water (4×5 L), saturated bicarbonate solution (2×5 L) and brine (5 L), then dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the title compound (2) as colorless liquid (400 g, 97% yield). The product was optionally 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