ethyl 4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]cyclohexane-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 100 mL round-bottom flask was charged ethyl 4-(2-tert-butoxy-2-oxoethyl)cyclohexanecarboxylate (Int-4b, 2.00 g, 7.40 mmol) and 4N HCl in 1,4-dioxane. The resulting solution was stirred at room temperature for 2 hours. At this point the solvent was removed in vacuo and the resulting residue was diluted with DCM and washed with H2O. The organic layer was dried over Na2SO4 and reduced in vacuo. The resulting residue was taken on without further purification. At this point the solvent was removed in vacuo the resulting residue was diluted with DCM washed with H2O The organic layer was dried over Na2SO4 The resulting residue was taken on without further purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 mL round-bottom flask was charged ethyl 4-(2-tert-butoxy-2-oxoethylidene)cyclohexanecarboxylate (Int-4a, 5.38 g, 19.90 mmol) followed by EtOAc (100 mL). The flask was flushed with argon and then 5% palladium on carbon was added. The flask was sealed and degassed under vacuum. H2 (g) was added in a balloon and the reaction was allowed to stir 18 hours under hydrogen atmosphere. After 18 hours, the reaction mixture was filtered through celite. The solvent was removed in vacuo and the resulting oil was taken on without further purification. The flask was flushed with argon 5% palladium on carbon was added The flask was sealed degassed under vacuum H2 (g) was added in a balloon After 18 hours the reaction mixture was filtered through celite The solvent was removed in vacuo the resulting oil was taken on without further purification