Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate → S-Tetrahydro-2H-pyran-4-YL ethanethioate

Temperature

50 °C

To a solution of 300 g (1.175 mol) of toluene-4-sulfonic acid tetrahydro-pyran-4-yl ester in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of NaI (0.12 g, 10 mol %) at room temperature. After complete addition, the reaction is heated to 50° C. for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2×2 L). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro-pyran-4-yl)ester. Yield: 81%; ES-MS: m/z 161 [M+H]; 1H-NMR (250 MHz, CHLOROFORM-d) δ ppm 1.47-1.98 (4 H, m), 2.30 (3 H, s), 3.41-3.74 (3 H, m), 3.88 (2 H, dt, J=11.76, 3.86 Hz)

1. additionAfter complete addition
2. customThe reaction mixture is partitioned between TBME (3 L) and water (3 L)
3. extractionthe aqueous layer is extracted with TBME (2 L)
4. extractionsaturated with NaCl and extracted again with TBME (2×2 L)
5. dry with materialThe combined organic extracts are dried over Na2SO4
6. filtrationfiltered
7. customthe solvent is removed under reduced pressure

ORD record

ord-62c0de0ff38c4677afb6738f950145d4

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315454B2