Tetrahydrofuran → HCID 24997071, compound

Participants

Reaction Steps

A solution of lithium aluminum hydride in THF (1.0M, 0.26 mL, 0.26 mmol) was diluted with diethyl ether (2 mL) and solid aluminum trichloride (0.098 g, 0.74 mmol) was added in portions. To the resulting solution was added a suspension of 9a-ethyl-6-methyl-8,9,9a,10-tetrahydroindeno[2,1-e]indazol-7(3H)-one (0.027 g, 0.10 mmol) in diethyl ether (1.5 mL). After 23 minutes, the reaction was quenched by the addition of EtOAc (0.5 mL) followed by 2N hydrochloric acid (0.5 mL). The reaction mixture was partitioned between EtOAc and water and the organic phase was washed with brine and dried over MgSO4. The solvent was evaporated under reduced pressure and the residue was chromatographed on silica gel (elution with 1:3 EtOAc/hexanes) to give 9a-ethyl-6-methyl-3,7,8,9,9a,10-hexahydroindeno[2,1-e]indazole.

Provenance & Evidence