Hydrochloric Acid → 1,2,3,5-Tetrahydro-6-methyl-s-indacene

Participants

Reaction Conditions

Reaction Steps

3.8 g (0.1 mol) of LiAlH4 was carefully added under cooling (0° C.) and stirring to the solution of 37.2 g (0.2 mol) of 2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one in 300 ml of Et2O. The resulting mixture was allowed to warm to room temperature and then was stirred overnight. Next day the mixture obtained was cooled to 0° C. and 10% HCl was carefully added. The organic phase was separated, dried over MgSO4. The 0.5 g of TSA was then added and the reaction mixture was refluxed in 1 h. After that it was washed by water solution of NaHCO3 and saturated water solution of NaCl. The organic phase was dried over MgSO4, evaporated and then isolated by distillation to give 28.5 g of the product (83%). B.p. 140° C./5 torr.

Provenance & Evidence