تفاعل #9356
ord-5a9e347455ad418da520a0da2e094ddc
معادلة التفاعل
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المعالجة
- 1استخلاصThe aqueous layer was extracted with CHCl3
- 2أخرىdried
- 3أخرىevaporated
- 4أخرىthe amide was used without further purification
- 5استخلاصextracted several times with CHCl3
- 6غسيلThe pooled fractions were washed with brine
- 7تجفيفdried over MgSO4
- 8ترشيحfiltered
- 9أخرىevaporated to dryness
- 10أخرىThe residue was purified by chromatography on SiO2
الإجراء التجريبي
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)