反応 #9356
ord-5a9e347455ad418da520a0da2e094ddc
反応方程式
反応条件
後処理
- 1抽出The aqueous layer was extracted with CHCl3
- 2その他dried
- 3その他evaporated
- 4その他the amide was used without further purification
- 5抽出extracted several times with CHCl3
- 6洗浄The pooled fractions were washed with brine
- 7乾燥dried over MgSO4
- 8ろ過filtered
- 9その他evaporated to dryness
- 10その他The residue was purified by chromatography on SiO2
実験手順
5,6,7,8-Tetrahydro-naphthalen-1-ylamine (Intermediate J1, commercially available from Aldrich) (5 mL, 35.3 mmol) was dissolved in CH2Cl2 (40 mL) and treated with NEt3 (10 mL) and acetyl chloride (3.8 mL, 53 mmol) at rt for 1 h. The mixture was diluted in CHCl3 and acidified with sat NH4Cl. The aqueous layer was extracted with CHCl3. The organic fractions were combined, dried and evaporated and the amide was used without further purification. The resulting amide (35.3 mmol) in acetone (450 mL) and aqueous MgSO4 (5 g in 28 mL) at 0° C. was treated with KMnO4 (16.8 g, 105 mmol). The mixture was allowed to stir at 0° C. for 2 h. The mixture was diluted with H2O and extracted several times with CHCl3. The pooled fractions were washed with brine and dried over MgSO4, filtered and evaporated to dryness. The residue was purified by chromatography on SiO2 to give N-(8-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl)-acetamide (Intermediate J2) as a yellow oil. (57%, in two 2 steps)