تفاعل #6494

معادلة التفاعل

DBU

Methyl 3-oxo-4-phenylbutyrate

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

product

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

DBU

→

title compound

المردود 65.0%

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

المردود 65.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirring continued overnight
2. 2
   أخرىThe reaction mixture was partitioned between diethyl ether and 1N aqueous hydrochloric acid solution (4:1)
3. 3
   استخلاصthe aqueous layer was extracted with diethyl ether
4. 4
   غسيلThe combined organic layers were washed with 1N aqueous hydrochloric acid and brine
5. 5
   تجفيفdried over anhydrous magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىThe residue was chromatographed on silica gel
9. 9
   غسيلeluted with hexane/ethyl acetate (6:1)

الإجراء التجريبي

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)+.

المصدر