تفاعل #42651
ord-0a8c163b372448ffabb1d46cac6b07e3
معادلة التفاعل
المتفاعلات
الكواشف
المذيبات
ظروف التفاعل
المعالجة
- 1أخرىthe ice bath was removed
- 2درجة الحرارةto warm to room temperature
- 3workup.STIRRINGstir for an additional 16 hours
- 4أخرىMost of the THF was removed by rotary evaporation in vacuo
- 5أخرىthe residue was partitioned between ethyl acetate and water
- 6غسيلThe organic layer was washed successively with water, sat. NH4Cl, water, sat. NaHCO3, water and brine
- 7تجفيفThe organic layer was dried over Na2SO4
- 8ترشيحfiltered
- 9أخرىevaporated under vacuum
- 10أخرىto give an off-white solid
- 11أخرىPurification by flash chromatography through a 1.6 kg column of silica gel eluting with 4% MeOH in dichloromethane
الإجراء التجريبي
A solution of (11β,16β)-9-fluoro-16-methyl-3,20-dioxo-11,17-bis[(trimethylsilyl)oxy]pregna-1,4-dien-21-yl acetate (26 g, ˜43 mmol) in 430 mL of tetrahydrofuran (THF) was cooled to 0° C. and neat acetic acid (4.95 mL, 86.5 mmol) was added followed by dropwise addition of a 1.0 M solution of tetra-n-butylammonium fluoride in THF (43.3 mL, 43.3 mmol). After stirring at 0° C. for 4 hours, the ice bath was removed and the reaction was allowed to warm to room temperature and stir for an additional 16 hours. Most of the THF was removed by rotary evaporation in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed successively with water, sat. NH4Cl, water, sat. NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and evaporated under vacuum to give an off-white solid. Purification by flash chromatography through a 1.6 kg column of silica gel eluting with 4% MeOH in dichloromethane provided 16.1 g of the title compound as a white solid.