Tetrahydrofuran → 2-Propenoic acid, 2-(phenylthio)ethyl ester

Temperature

-30 °C

To a 500 mL three-neck round bottom flask equipped with mechanical stirrer were charged 2-hydroxyethyl phenyl sulfide (33.0 g, 0.21 mol), anhydrous triethylamine (45 mL, 0.32 mol), and anhydrous tetrahydrofuran (160 mL). The solution was cooled in a −30° C. acetone/dry ice bath under nitrogen blanket for 15 mins. Acryloyl chloride (22 mL, 0.27 mol) was added into the vigorously stirred cold solution through an addition funnel over 30 min. After the addition, the reaction mixture was stirred in the cold acetone bath for additional four hours followed by quenching with the addition of 2M HCl (200 mL). The mixture was extracted with diether ether (150 mL×3) and the combined organic layer was washed with DI water (200 mL×3), aqueous sodium bicarbonate (200 mL×2), and dried over MgSO4. Filtration and removal of solvents under reduced pressure gave the crude product as a light brown oil which was purified on silica gel using Hexanes/Ethyl acetate (50/1, v/v) as eluent to give the final product as a colorless oil (27.4 g, 0.13 mol, yield: 62%), H1 NMR (CDCl3): δ 7.44 (2H), 7.33 (2H), 7.24 (1H), 6.41 (1H), 6.12 (1H), 5.85 (1H), 4.35 (2H), 3.21 (2H).

1. customTo a 500 mL three-neck round bottom flask equipped with mechanical stirrer
2. additionAfter the addition
3. customby quenching with the addition of 2M HCl (200 mL)
4. extractionThe mixture was extracted with diether ether (150 mL×3)
5. washthe combined organic layer was washed with DI water (200 mL×3), aqueous sodium bicarbonate (200 mL×2)
6. dry with materialdried over MgSO4
7. filtrationFiltration and removal of solvents under reduced pressure
8. customgave the crude product as a light brown oil which
9. customwas purified on silica gel

ORD record

ord-36ca6b3f53e84ffaad2bac7cdf044404

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969429B2