Sodium Hydroxide → HCID 68908424, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of E/Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one (0.50 g, 1.72 mmol) and [(E)-3-(2,2-Dimethylpropoxy)-1-methyleneallyloxy]trimethylsilane (1.1 g, 5.5 mmole) in a sealed tube was heated to 150° C. for 1.5 hrs. The reaction mixture was diluted with MeOH (10 mL) and treated with 2.0 mL of 4 N NaOH at rt for 1 h. The mixture was then diluted with AcOEt and washed with Sat NH4Cl, brine, dried over Na2SO4. After concentration the residue was purified by flash column (2%-25% AcOEt in Hex) to give rac-(1R,2S,6R)-6′-chloro-2-(3-chlorophenyl)-6-(2,2-dimethylpropoxy)-spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (310.4 mg, 43.1%) and rac-(1R,2S)-6′-chloro-2-(3-chlorophenyl)spiro[5-cyclohexene-1,3′-[3H]indole]-2′,4(1′H)-dione (201.2 mg, 32.3%).

Provenance & Evidence