반응 #7966

반응 방정식

(2RS,9aSR)-9a-butyl-7-methoxymethoxy-4-methyl-2-(2-oxoethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HCl

→

(2RS,9aSR)-9a-butyl-7-hydroxy-4-methyl-2-(2-oxoethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one

수율 67.1%

용매

EtOAc

methanol

반응 조건

후처리

1. 1
   온도by heating in an oil bath at 80° C. for 40 minutes
2. 2
   온도On cooling to room temperature
3. 3
   기타crystals formed
4. 4
   세척washed with 5% NaHCO3 and 1N HCl
5. 5
   추출The aqueous washes were back-extracted with EtOAc
6. 6
   세척The combined organics were washed with brine
7. 7
   건조dried over MgSO4
8. 8
   여과filtered
9. 9
   농축concentrated under vacuum
10. 10
    기타The residue was purified by PLC on a 0.1×20×20 cm silica gel GF plate

실험 절차

A solution of (2RS,9aSR)-9a-butyl-7-methoxymethoxy-4-methyl-2-(2-oxoethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (85 mg) in methanol (1 mL) was diluted with 2N HCl (0.36 mL, 0.72 mmol). The resulting mixture was stirred at room temperature for 30 minutes followed by heating in an oil bath at 80° C. for 40 minutes. On cooling to room temperature, crystals formed. The mixture was diluted with EtOAc and washed with 5% NaHCO3 and 1N HCl. The aqueous washes were back-extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by PLC on a 0.1×20×20 cm silica gel GF plate, using 2:1 hexanes-EtOAc as developing solvent, to afford (2RS,9aSR)-9a-butyl-7-hydroxy-4-methyl-2-(2-oxoethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (50 mg).

출처