Acetone → Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide

To a solution of tetrahydrothiopyran-3-ol-1,1-dioxide (7.5 g, 0.05 moles) and acetone (150 mL) was slowly added enough Jones reagent to maintain a brown color for at least 10 minutes without need for additional reagent. The excess reagent was reduced by addition of isopropanol (5 mL). The mixture was filtered through anhydrous magnesium sulfate and the chromium salts were washed 3× with acetone. The solvent was removed in vacuo to give a solid which was triturated with ethanol. The resulting crystals were isolated by filtration and rinsed 3× with diethyl ether. After drying, 5.0 g of product was obtained. H' NMR CDCl3 4.0 (singlet, 2H) 3.3 (triplet, 2H) 2.6 (triplet, 2H) 2.3 (multiplet, 2H).

1. temperatureto maintain a brown color for at least 10 minutes without need for additional reagent
2. filtrationThe mixture was filtered through anhydrous magnesium sulfate
3. washthe chromium salts were washed 3× with acetone
4. customThe solvent was removed in vacuo
5. customto give a solid which
6. customwas triturated with ethanol
7. customThe resulting crystals were isolated by filtration
8. washrinsed 3× with diethyl ether
9. customAfter drying

ORD-Eintrag

ord-d266dfb256b7486bb2b480c2d3beb8b1

Quelldatensatz

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04777167