Carbonothioic acid, O-(1-chloroethyl) S-ethyl ester → 1-{[(Ethylthio)carbonyl]oxy}ethyl 2-methylpropionate

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).

1. customthe solvent removed in vacuo
2. dissolutionThe residue was dissolved in diethyl ether (600 mL)
3. washwashed with water (3×300 mL)
4. customthe organic phase was separated
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. distillationThe residue was purified by vacuum distillation (60° C./240 mTorr)

ORD-Eintrag

ord-acc15745391840cca3569b2dd8f990c4

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08378137B2