반응 #7955
ord-95e98eaea1a94f0591c92261b6aa3074
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후처리
- 1workup.ADDITIONwas added by syringe
- 2온도to slowly warm to room temperature
- 3workup.STIRRINGstirred at room temperature overnight
- 4추출The aqueous phase was extracted with more EtOAc (20 mL)
- 5세척The combined organics were washed with 5% NaHCO3, water, and brine
- 6건조dried over MgSO4
- 7여과filtered
- 8농축concentrated under vacuum to a yellow oil
- 9기타The crude product was purified by preparative layer chromatography (PLC) on a 0.1×20×20 cm silica gel GF plate
- 10추출The band at Rf 0.44-0.56 was extracted with EtOAc
- 11기타the extracts evaporated under vacuum
실험 절차
A solution of 9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (162 mg, 0.52 mmol) in anhydrous THF (2.5 mL) was cooled in an ice bath and stirred under a nitrogen atmosphere while 0.4M LDA in THF (1.55 mL, 0.62 mmol) was added by syringe. After stirring at 0° C. for 30 minutes, the solution was cooled to −78° C. (dry ice-acetone bath) and treated with iodomethane (0.162 mL, 2.6 mmol). The resulting mixture was allowed to slowly warm to room temperature, then stirred at room temperature overnight. The mixture was diluted with EtOAc (60 mL) and shaken with saturated aqueous NH4Cl (40 mL). The aqueous phase was extracted with more EtOAc (20 mL). The combined organics were washed with 5% NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated under vacuum to a yellow oil. The crude product was purified by preparative layer chromatography (PLC) on a 0.1×20×20 cm silica gel GF plate using 4:1 hexanes-EtOAc as developing solvent. The band at Rf 0.44-0.56 was extracted with EtOAc and the extracts evaporated under vacuum to provide (2SR,9aSR)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (111 mg) as an oil.