반응 #6494

반응 방정식

DBU

Methyl 3-oxo-4-phenylbutyrate

1-cyano-6-methoxy-3,4-dihydronaphthalene

product

1-Cyano-6-methoxy-3,4-dihydronaphthalene

DBU

→

title compound

수율 65.0%

Methyl 3-oxo-4-phenyl-2-(1-cyano-6-methoxy-1,2,3,4-tetrahydronaphth-2-yl)-butyrate

수율 65.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   workup.STIRRINGstirring continued overnight
2. 2
   기타The reaction mixture was partitioned between diethyl ether and 1N aqueous hydrochloric acid solution (4:1)
3. 3
   추출the aqueous layer was extracted with diethyl ether
4. 4
   세척The combined organic layers were washed with 1N aqueous hydrochloric acid and brine
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was chromatographed on silica gel
9. 9
   세척eluted with hexane/ethyl acetate (6:1)

실험 절차

Methyl 3-oxo-4-phenylbutyrate (29.33 g, 153 mmol) and 1-cyano-6-methoxy-3,4-dihydronaphthalene (25.7, 139 mmol), the product of Step 2 of Example 1, were dissolved in 25 mL of acetonitrile. DBU (1.5 mL) was added and the reaction mixture was stirred for 2 h at ambient temperature. A second aliquot of DBU (1.5 mL) was then added and stirring continued overnight. The reaction mixture was partitioned between diethyl ether and 1N aqueous hydrochloric acid solution (4:1) and the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with 1N aqueous hydrochloric acid and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel eluted with hexane/ethyl acetate (6:1) to give 33.9 g (65% yield) of the title compound; MS DCl--NH3M/Z: 395 (M+NH4)+.

출처