Water → 4-(Acetylthiomethyl)tetrahydropyran

Temperature

70 °C

To 224 g (0.83 mol) of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester in methyl isobutylketone (1.6 L) are added 189 g (1.66 mol) of potassium thioacetate. The suspension is stirred at 70° C. for 4.5 h. The reaction mixture is cooled to RT and water (1.8 L) is added. The organic layer is washed with 10% aq. K2CO3 solution (1.8 L) and water (1 L). The organic layer is filtered through Celite® (20 g), activated charcoal (20 g) and Na2SO4 (20 g) and the filtrate is concentrated under reduced pressure. The residual oil is azeotroped with methylcyclohexane (200 mL) and n-heptanes (250 mL) to afford 138 g of thioacetic acid S-(tetrahydro-pyran-4-ylmethyl) ester. Yield: 96%; ESI-MS: 175 [M+H]+

1. temperatureThe reaction mixture is cooled to RT
2. washThe organic layer is washed with 10% aq. K2CO3 solution (1.8 L) and water (1 L)
3. filtrationThe organic layer is filtered through Celite® (20 g), activated charcoal (20 g) and Na2SO4 (20 g)
4. concentrationthe filtrate is concentrated under reduced pressure
5. customThe residual oil is azeotroped with methylcyclohexane (200 mL) and n-heptanes (250 mL)

ORD record

ord-bdba0048fabe40588e164281e7923365

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865744B1