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

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of ethyl 4-(2-tert-butoxy-2-oxoethylidene)cyclohexanecarboxylate (5.3 g, 21 mmol) in CH2Cl2 (30 ml) was added TFA (30 ml). The solution was stirred at room temperature overnight. The solution was concentrated in vacuo to afford 6 g of product as colorless oil, which was used directly for next step without further purification. The solution was concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of anhydrous lithium chloride (1.9 g, 45 mmol) in MeCN (100 ml) was added tert-butyl 2-(diethoxyphosphoryl)acetate (7.6 g, 30 mmol) at room temperature. The mixture was stirred for 30 min. TEA (6.4 ml, 45 mmol) was added and the mixture was stirred for another 30 min. Ethyl 4-oxocyclohexanecarboxylate (5.1 g, 30 mmol) was added and the mixture was stirred overnight. The precipitate was filtered off and the filtrate was concentrated to afford brown oil, which was purified by silica gel column (PE:EtOAc=10:1) to afford product (5 g, 62%). the mixture was stirred for another 30 min the mixture was stirred overnight The precipitate was filtered off the filtrate was concentrated to afford brown oil, which was purified by silica gel column (PE:EtOAc=10:1)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of ethyl 4-(2-tert-butoxy-2-oxoethylidene)cyclohexanecarboxylate (5.3 g, 21 mmol) in CH2Cl2 (30 ml) was added TFA (30 ml). The solution was stirred at room temperature overnight. The solution was concentrated in vacuo to afford 6 g of product as colorless oil, which was used directly for next step without further purification. The solution was concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of anhydrous lithium chloride (1.9 g, 45 mmol) in MeCN (100 ml) was added tert-butyl 2-(diethoxyphosphoryl)acetate (7.6 g, 30 mmol) at room temperature. The mixture was stirred for 30 min. TEA (6.4 ml, 45 mmol) was added and the mixture was stirred for another 30 min. Ethyl 4-oxocyclohexanecarboxylate (5.1 g, 30 mmol) was added and the mixture was stirred overnight. The precipitate was filtered off and the filtrate was concentrated to afford brown oil, which was purified by silica gel column (PE:EtOAc=10:1) to afford product (5 g, 62%). the mixture was stirred for another 30 min the mixture was stirred overnight The precipitate was filtered off the filtrate was concentrated to afford brown oil, which was purified by silica gel column (PE:EtOAc=10:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of ethyl 4-(2-tert-butoxy-2-oxoethylidene)cyclohexanecarboxylate (5.3 g, 21 mmol) in CH2Cl2 (30 ml) was added TFA (30 ml). The solution was stirred at room temperature overnight. The solution was concentrated in vacuo to afford 6 g of product as colorless oil, which was used directly for next step without further purification. The solution was concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of anhydrous lithium chloride (1.9 g, 45 mmol) in MeCN (100 ml) was added tert-butyl 2-(diethoxyphosphoryl)acetate (7.6 g, 30 mmol) at room temperature. The mixture was stirred for 30 min. TEA (6.4 ml, 45 mmol) was added and the mixture was stirred for another 30 min. Ethyl 4-oxocyclohexanecarboxylate (5.1 g, 30 mmol) was added and the mixture was stirred overnight. The precipitate was filtered off and the filtrate was concentrated to afford brown oil, which was purified by silica gel column (PE:EtOAc=10:1) to afford product (5 g, 62%). the mixture was stirred for another 30 min the mixture was stirred overnight The precipitate was filtered off the filtrate was concentrated to afford brown oil, which was purified by silica gel column (PE:EtOAc=10:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of ethyl 4-(2-tert-butoxy-2-oxoethylidene)cyclohexanecarboxylate (5.3 g, 21 mmol) in CH2Cl2 (30 ml) was added TFA (30 ml). The solution was stirred at room temperature overnight. The solution was concentrated in vacuo to afford 6 g of product as colorless oil, which was used directly for next step without further purification. The solution was concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of anhydrous lithium chloride (1.9 g, 45 mmol) in MeCN (100 ml) was added tert-butyl 2-(diethoxyphosphoryl)acetate (7.6 g, 30 mmol) at room temperature. The mixture was stirred for 30 min. TEA (6.4 ml, 45 mmol) was added and the mixture was stirred for another 30 min. Ethyl 4-oxocyclohexanecarboxylate (5.1 g, 30 mmol) was added and the mixture was stirred overnight. The precipitate was filtered off and the filtrate was concentrated to afford brown oil, which was purified by silica gel column (PE:EtOAc=10:1) to afford product (5 g, 62%). the mixture was stirred for another 30 min the mixture was stirred overnight The precipitate was filtered off the filtrate was concentrated to afford brown oil, which was purified by silica gel column (PE:EtOAc=10:1)