Reaction #632032

Reaction equation

( 13 )

Tetramethylammonium Isobutyrate

isobutyric acid

( 12 )

O-(1-Chloroisobutoxy) S-Methyl Thiocarbonate

→

title compound ( 11 )

Yield 67.7%

O-(1-Isobutanoyloxyisobutoxy) S-Methyl Thiocarbonate

Yield 67.7%

Solvents

EtOAc

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to 20° C.
2. 2
   Washwashed with water (2×1 L), saturated NaHCO3 (1×2 L) and water (1 L)
3. 3
   OtherThe organic phase was separated
4. 4
   Concentrationconcentrated under reduced pressure

Procedure

To a 3 L three neck round bottom flask equipped with a mechanical stirrer and Teflon-coated thermocouple was added (13) (1672 g, 9 mol), isobutyric acid (264 g, 1.5 mol), and (12) (1050 g, 5.76 mol). The reaction mixture was heated to 80° C. for 12 h, monitoring the reaction progress by 1H NMR. The reaction mixture was cooled to 20° C., diluted with EtOAc (1 L) and washed with water (2×1 L), saturated NaHCO3 (1×2 L) and water (1 L). The organic phase was separated and concentrated under reduced pressure to afford the title compound (11) (905 g, 3.9 mol, 65% yield) as a colorless liquid. 1H NMR (CDCl3, 400 MHz): δ 1.0 (d, 6H), 1.2 (dd, 6H), 2.05 (m, 1H), 2.35 (s, 3H), 2.6 (m, 1H), 6.7 (d, 1H).

Source