반응 #7959

반응 방정식

9a-butyl-7-methoxymethoxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HCl

NaHCO3

→

9a-butyl-7-hydroxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

용매

methanol

EtOAc

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   기타The aqueous portion was separated
3. 3
   추출extracted with EtOAc (40 mL)
4. 4
   세척The combined organics were washed with water and brine
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   농축concentrated under vacuum to an oil
8. 8
   기타The crude product was purified by PLC on a 0.1×20×20 cm silica gel GF plate
9. 9
   세척The band at Rf 0.34-0.43 was eluted with EtOAc
10. 10
    기타the eluant evaporated under vacuum to a residue which

실험 절차

A solution of 9a-butyl-7-methoxymethoxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (28 mg, 0.08 mmol) in methanol (2 mL) was placed under a nitrogen atmosphere and treated with 2N aqueous HCl (0.12 mL, 0.24 mmol). The resulting yellow solution was stirred and heated in an oil bath at 55-80° C. for 45 minutes. After cooling to room temperature, the mixture was diluted with EtOAc (60 mL) and shaken with 5% aqueous NaHCO3. The aqueous portion was separated and extracted with EtOAc (40 mL). 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 4:1 hexanes-EtOAc. The band at Rf 0.34-0.43 was eluted with EtOAc and the eluant evaporated under vacuum to a residue which was lyophilized from benzene to afford 9a-butyl-7-hydroxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.

출처