Reaktion #2350796

Reaktionsgleichung

Potassium thioacetate

1,4-dioxaspiro[4.5]dec-8-yl methanesulfonate

→

1,4-dioxaspiro[4.5]dec-8-yl ethanethioate

Ausbeute 64.8%

Lösungsmittel

brine

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe combined organic fractions were washed with brine
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by column chromatography on silica gel using a Biotage 65i cartridge
7. 7
   Wascheneluting with EtOAc/isohexane

Vorschrift

Potassium thioacetate (21.39 g, 187 mmol) was added to a stirred mixture of 1,4-dioxaspiro[4.5]dec-8-yl methanesulfonate (29.5 g, 125 mmol) in DMSO (31.2 ml) and the mixture was heated at 40° C. for 24 h. The mixture was cooled, brine was added and the mixture was extracted with ethyl acetate. The combined organic fractions were washed with brine, dried, and evaporated. The residue was purified by column chromatography on silica gel using a Biotage 65i cartridge, eluting with EtOAc/isohexane to give 1,4-dioxaspiro[4.5]dec-8-yl ethanethioate (17.5 g, 81 mmol, 64.8% yield) as a red oil. 1H NMR (500 MHz, CDCl3): δ 3.92 (4H, s), 3.53 (1H, s), 2.29 (3H, s), 2.00-1.93 (2H, m), 1.77-1.63 (6H, m).

Quelle