Reaktion #7961

Reaktionsgleichung

(2SR,9aRS)-9a-butyl-2-iodo-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HCl

NaHCO3

→

(2SR,9aRS)-9a-butyl-7-hydroxy-2-iodo-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Lösungsmittel

methanol

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated in an oil bath at 70° C. for 50 minutes
2. 2
   TemperaturAfter cooling to room temperature
3. 3
   SonstigeThe aqueous portion was separated
4. 4
   Extraktionextracted with EtOAc
5. 5
   WaschenThe combined organics were washed with water and brine
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under vacuum to an oil
9. 9
   SonstigeThe crude product was purified by PLC on a 0.1×20×20 cm silica gel GF plate
10. 10
    WaschenThe band at Rf 0.24-0.32 was eluted with EtOAc
11. 11
    Sonstigethe eluant evaporated under vacuum

Vorschrift

A suspension of (2SR,9aRS)-9a-butyl-2-iodo-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (50 mg, 0.11 mmol) in methanol (3.5 mL) was placed under a nitrogen atmosphere, heated in an oil bath at 70° C. to affect solution, then treated with 2N aqueous HCl (0.195 mL, 0.39 mmol). The resulting solution was stirred and heated in an oil bath at 70° C. for 50 minutes. After cooling to room temperature, the mixture was diluted with EtOAc and shaken with 5% aqueous NaHCO3. The aqueous portion was separated and extracted with EtOAc. The combined organics were washed with water and brine, dried over MgSO4, filtered, and concentrated under vacuum to an oil. The crude product was purified by PLC on a 0.1×20×20 cm silica gel GF plate, developing twice with 5:1 hexanes-EtOAc. The band at Rf 0.24-0.32 was eluted with EtOAc and the eluant evaporated under vacuum to provide (2SR,9aRS)-9a-butyl-7-hydroxy-2-iodo-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an oil.

Quelle