تفاعل #7954
ord-3748d7f80bee42f6a817e582c782f3ac
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
ظروف التفاعل
المعالجة
- 1workup.STIRRINGThe resulting mixture was stirred
- 2workup.STIRRINGAfter stirring an additional 25 minutes at room temperature
- 3غسيلwashed with 1.3N HCl (1 L)
- 4أخرىThe aqueous phase was separated
- 5استخلاصextracted with EtOAc (200 mL)
- 6غسيلThe combined organics were washed with 5% NaHCO3 (500 ml) and brine
- 7تجفيفdried over MgSO4
- 8ترشيحfiltered
- 9تركيزconcentrated under vacuum to an orange oil (6.5 g)
- 10أخرىeach purified by flash chromatography on silica gel using Biotage FLASH 40M columns and 10:1 hexanes-EtOAc
- 11غسيلas eluting solvent
- 12workup.ADDITIONThe product containing fractions
- 13أخرىevaporated under vacuum
الإجراء التجريبي
A solution of 9a-butyl-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (5.30 g, 21 mmol) in anhydrous dimethylformamide (50 mL) was cooled in an ice bath, stirred under a nitrogen atmosphere, and treated successively with N,N-diisopropyl-ethylamine (10.5 mL, 60 mmol) and chloromethyl methyl ether (3.45 mL, 41 mmol). The resulting mixture was stirred while gradually warming to room temperature over 5 hours. After 5.5 hours, additional N,N-diisopropyl-ethylamine (3 mL) and chloromethyl methyl ether (1 mL) were added. After stirring an additional 25 minutes at room temperature, the reaction mixture was diluted with EtOAc (1 L) and washed with 1.3N HCl (1 L). The aqueous phase was separated and extracted with EtOAc (200 mL). The combined organics were washed with 5% NaHCO3 (500 ml) and brine, dried over MgSO4, filtered, and concentrated under vacuum to an orange oil (6.5 g). This material was divided into three portions and each purified by flash chromatography on silica gel using Biotage FLASH 40M columns and 10:1 hexanes-EtOAc as eluting solvent. The product containing fractions were combined and evaporated under vacuum to afford 9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (4.98 g) as an oil.