Reaktion #962443

Reaktionsgleichung

Tosyl chloride

pyridine

Compound

(5aR,9bS)-3,3a-Dihydroxy-3-(hydroxymethyl)-5a,9-dimethyl-3,3a,4,5,5a,6,7,8-octahydronaphtho[1,2-b]furan-2(9bH)-one

→

title compound

((5aR,9bS)-3,3a-Dihydroxy-5a,9-dimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydronaphtho[1,2-b]furan-3-yl)methyl 4-methylbenzenesulfonate

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction mixture
2. 2
   Extraktionwas extracted with dichloromethane (5 mL)
3. 3
   SonstigeDichloromethane was removed
4. 4
   Sonstigecrude product was purified by column chromatography (silica gel, 5-10% ethyl acetate in petroleum ether)

Vorschrift

Compound of example 2 (126.6 mg, 0.449 mmol) was dissolved in dichloromethane (5 mL). Tosyl chloride (427.9 mg, 2.24 mmole), pyridine (355.05 mg, 4.48 mmole) and DMAP (2 mg) were added to this solution and reaction mixture was stirred for 72 hours. Reaction mixture was extracted with dichloromethane (5 mL). Dichloromethane was removed and crude product was purified by column chromatography (silica gel, 5-10% ethyl acetate in petroleum ether) to obtain the title compound.

Quelle