反应详情

Cyclopropanecarbonitrile (17.14 g) was added dropwise to a mixture of lithium diisopropylamide solution (2M in a mixture of heptane, tetrahydrofuran and ethylbenzene; 128 ml), 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (30 ml) and tetrahydrofuran (240 ml) stirring at -78° C. under nitrogen. Stirring was continued for 1 hour at this temperature then a solution of 1-chlorotetralin (48.4 g) in tetrahydrofuran (50 ml) was added slowly and after a further hour the solution was allowed to warm to ambient temperature, then was heated under gentle reflux for 2 hours. The solvent was removed in vacuo and the residue acidified with concentrated hydrochloric acid then extracted with ethyl acetate (4×100 ml). The combined extracts were dried over magnesium sulphate and the solvent removed in vacuo to leave a semi-solid which was filtered and washed with acetonitrile, then recrystallised from acetone to give 1-(1,2,3,4-tetrahydronaphth-1-yl)cyclopropanecarbonitrile (8.3 g), mp 91°-93° C.

1. temperaturewas heated
2. temperatureunder gentle reflux for 2 hours
3. customThe solvent was removed in vacuo
4. extractionthen extracted with ethyl acetate (4×100 ml)
5. dry with materialThe combined extracts were dried over magnesium sulphate
6. customthe solvent removed in vacuo
7. customto leave a semi-solid which
8. filtrationwas filtered
9. washwashed with acetonitrile
10. customrecrystallised from acetone