反应 #9356

反应方程式

NH4Cl

acetyl chloride

MgSO4

KMnO4

5,6,7,8-Tetrahydro-naphthalen-1-ylamine

→

N-(8-oxo-5,6,7,8-tetrahydro-naphthalen-1-yl)-acetamide

溶剂

CHCl3

NEt3

H2O

acetone

CH2Cl2

反应条件

后处理

1. 1
   萃取The aqueous layer was extracted with CHCl3
2. 2
   其他dried
3. 3
   其他evaporated
4. 4
   其他the amide was used without further purification
5. 5
   萃取extracted several times with CHCl3
6. 6
   洗涤The pooled fractions were washed with brine
7. 7
   干燥dried over MgSO4
8. 8
   过滤filtered
9. 9
   其他evaporated to dryness
10. 10
    其他The residue was purified by chromatography on SiO2

实验过程

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)

来源