Réaction #476534

Équation de réaction

tetrabutylammonium isobutyrate

Tetrabutylammonium Isobutyrate

compound ( 2 )

O-(1-Chloroethyl) S-Ethyl Thiocarbonate

→

product ( 7 )

Rendement 63.0%

O-(1-Isobutanoyloxyethyl) S-Ethyl Thiocarbonate

Rendement 63.0%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autrethe solvent removed in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in diethyl ether (600 mL)
3. 3
   Lavagewashed with water (3×300 mL)
4. 4
   Autrethe organic phase was separated
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo
8. 8
   workup.DISTILLATIONThe residue was purified by vacuum distillation (60° C./240 mTorr)

Mode opératoire

To a solution of tetrabutylammonium isobutyrate (5) (382 mmol) in tetrahydrofuran (500 mL) was added compound (2) (49 g, 288 mmol). The mixture was stirred at ambient temperature for 16 h then the solvent removed in vacuo. The residue was dissolved in diethyl ether (600 mL), washed with water (3×300 mL) and the organic phase was separated, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by vacuum distillation (60° C./240 mTorr) to afford the product (7) as a colorless liquid (40 g, 63%). 1H NMR (CDCl3, 400 MHz): δ 1.2 (d, 6H), 1.35 (t, 3H), 1.5 (d, 3H), 1.55 (m, 1H), 2.85 (dq, 2H), 6.95 (q, 1H).

Source