反应详情

The mixture of 3,5,6,7-tetrahydro-s-indacen-1(2H)-one (12.4 g, 0.072 mol), p-toluenesulfonyl hydrazide (13.4 g, 0.072 mol), 0.5 g TSA and i-propanol (100 ml) was refluxed by 5 min, and cooled to room temperature. Precipitate was filtered, washed by MeOH and dried, given 21 g of product (90%). Suspension of obtained hydrazone in 250 ml abs. Et2O was cooled to −70° C. and was treated with 15% n-butyllithium in hexane (100 ml. 0.16 mol). The resulting mixture was allowed to warm up to r.t. and refluxed until gas evolution. Reaction mixture was treated with 50 ml NH4Cl (10%), washed by water and dried. Solvent was evaporated, the residue was extracted by hot hexane, and to give after evaporation 9.1 g of solid product (81%).

1. temperaturewas refluxed by 5 min
2. filtrationPrecipitate was filtered
3. washwashed by MeOH
4. customdried
5. additionSuspension of obtained hydrazone in 250 ml abs
6. temperatureEt2O was cooled to −70° C.
7. temperatureto warm up to r.t.
8. temperaturerefluxed until gas evolution
9. customReaction mixture
10. washwashed by water
11. customdried
12. customSolvent was evaporated
13. extractionthe residue was extracted by hot hexane
14. customto give
15. customafter evaporation 9.1 g of solid product (81%)