تفاعل #7964
ord-6135e02ccc8a47dd9175ba392412cef1
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1workup.STIRRINGThe resulting solution was stirred at 0° C. for 30 minutes
- 2workup.STIRRINGthen stirred at room temperature overnight
- 3استخلاصThe aqueous phase was extracted with EtOAc (20 mL)
- 4غسيلthe combined organics were washed with 5% NaHCO3 and brine
- 5تجفيفdried over MgSO4
- 6ترشيحfiltered
- 7تركيزconcentrated under vacuum to a yellow oil
- 8أخرىThe crude product was purified by preparative layer chromatography on three 0.1×20×20 silica gel GF plates
- 9غسيلThe UV visible band at Rf 0.44-0.56 was eluted with EtOAc
- 10أخرىthe eluant evaporated under vacuum
الإجراء التجريبي
A solution of 9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (230 mg, 0.73 mmol) in anhydrous THF (3.8 mL) was cooled in an ice bath, stirred under a nitrogen atmosphere, and treated with freshly prepared 0.4M LDA in THF (2.2 mL, 0.88 mmol). The resulting solution was stirred at 0° C. for 30 minutes, then cooled to −78° C. (dry ice-acetone bath) and treated with allyl bromide (0.316 mL, 3.65 mmol). The reaction mixture was allowed to gradually warm to room temperature then stirred at room temperature overnight. The mixture was diluted with EtOAc (60 mL) and shaken with 1N HCl (35 mL). The aqueous phase was extracted with EtOAc (20 mL) and the combined organics were washed with 5% NaHCO3 and brine, dried over MgSO4, filtered, and concentrated under vacuum to a yellow oil. The crude product was purified by preparative layer chromatography on three 0.1×20×20 silica gel GF plates using 4:1 hexanes-EtOAc as developing solvent. The UV visible band at Rf 0.44-0.56 was eluted with EtOAc and the eluant evaporated under vacuum to afford (2SR,9aSR)-2-allyl-9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (193 mg) as an oil.