反応 #7967

反応方程式

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

NaBH4

→

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

溶媒

2-propanol

反応条件

後処理

1. 1
   その他The solvent was evaporated under vacuum
2. 2
   洗浄washed with 0.2N HCl (30 mL), 5% NaHCO3, and brine
3. 3
   乾燥dried over MgSO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated under vacuum to a gum (24 mg)
6. 6
   その他This material was purified by PLC on a 0.1×20×20 cm silica gel GF plate

実験手順

A solution of (2RS,9aSR)-9a-butyl-7-hydroxy-4-methyl-2-(2-oxo-ethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (17 mg, 0.05 mmol) in 2-propanol (2 mL) was treated with NaBH4 (1.9 mg, 0.05 mmol) and the mixture was stirred at room temperature for 40 minutes. The solvent was evaporated under vacuum. The residue was taken up in EtOAc (60 mL), washed with 0.2N HCl (30 mL), 5% NaHCO3, and brine, dried over MgSO4, filtered, and concentrated under vacuum to a gum (24 mg). This material was purified by PLC on a 0.1×20×20 cm silica gel GF plate using 2:1 hexanes-EtOAc as developing solvent. The UV visible band at Rf 0.06-0.11 afforded (2RS,9aSR)-9a-butyl-7-hydroxy-2-(2-hydroxyethyl)-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an oil.

出典