反应 #155326

反应方程式

8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one

sodium iodide

sodium hydride

di-tert-butyl chloromethyl phosphate

→

di-tert-butyl 8-(4-methoxyphenyl)-9-oxo-5-propoxy-1,2,3,9-tetrahydro-6-aza-cyclopenta[a]naphthalen-6-ylmethyl phosphate

收率 40.0%

溶剂

DMF

DMF

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was then stirred at 40° C. for 4 hours
2. 2
   温度cooled
3. 3
   萃取the reaction mixture was subjected to extraction
4. 4
   洗涤The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
5. 5
   干燥dried over anhydrous sodium sulfate
6. 6
   浓缩concentrated under reduced pressure
7. 7
   其他The residue was purified
8. 8
   浓缩The purified product was concentrated under reduced pressure

实验过程

To a DMF solution (10 ml) of 8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one (400 mg, 1.15 mmol) and sodium iodide (343 mg, 2.29 mmol) was added sodium hydride (60% oil base, 74.9 mg, 1.72 mmol), and the mixture was then stirred for 10 minutes at room temperature. To the resulting mixture was added a DMF solution (20 ml) of di-tert-butyl chloromethyl phosphate (888 mg, 3.43 mmol), and the mixture was then stirred at 40° C. for 4 hours. The reaction mixture was ice-cooled, ice water was added thereto, and then the reaction mixture was subjected to extraction using ethyl acetate. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified using medium pressure liquid chromatography (NH silica gel, n-hexane:ethyl acetate=100:0→0:100). The purified product was concentrated under reduced pressure, giving a white powder of di-tert-butyl 8-(4-methoxyphenyl)-9-oxo-5-propoxy-1,2,3,9-tetrahydro-6-aza-cyclopenta[a]naphthalen-6-ylmethyl phosphate (263 mg, yield: 40%).

来源