反応 #52538

反応方程式

methyl [4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate

Compound 4

methyl [4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate

NaBH4

→

title compound

収率 87.0%

Methyl[4-(5-hydroxy-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate

収率 87.0%

溶媒

MeOH

反応条件

後処理

1. 1
   その他quenched by the addition of H2O
2. 2
   workup.ADDITIONThe solution was diluted with Et2O
3. 3
   洗浄washed with H2O and saturated aqueous NaCl
4. 4
   乾燥before being dried (MgSO4)
5. 5
   その他the solvents were removed under reduced pressure

実験手順

To a solution of methyl [4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl-ethynyl)-phenyl]-acetate (Compound 4) in 5 mL MeOH at 0° C. was added NaBH4 (18.0 mg, 0.48 mmol). The reaction was stirred at 0° C. for 2 hours and then quenched by the addition of H2O. The solution was diluted with Et2O and washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and the solvents were removed under reduced pressure. Column chromatography (20-40% EtOAc—hexanes) afforded 140.0 mg (87%) of the title compound as a colorless oil.

出典