1-(oxan-4-yl)propan-2-one

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

Procedure: The method described in Part B of Example 3 was repeated with 1-tetrahydro-4H-pyran-4-ylideneacetone (4.0 g, 28.5 mmol), and the resulting 1-tetrahydro-2H-pyran-4-ylacetone was mixed with diethyl oxalate (4.66 g, 31.9 mmol) and added to a solution of sodium tert-butoxide (3.07 g, 31.9 mmol) in ethanol (22 mL). The reaction was carried out according to the method described in Part C of Example 3 with the following modifications. Hydroxyethylhydrazine (2.43 g, 31.9 mmol) was used instead of ethylhydrazine oxalate. Extractions were carried out seven times with chloroform, and the crude product was not purified. Ethyl 1-(2-hydroxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxylate (8.2 g) was obtained as a viscous yellow oil. Extractions the crude product was not purified

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

Procedure: A solution of 1-tetrahydro-4H-pyran-4-ylideneacetone (4.0 g, 28.5 mmol) in ethyl acetate was added to a Parr vessel. The vessel was purged with nitrogen, and 10% palladium on carbon (400 mg) was added. The vessel was shaken under hydrogen pressure (50 psi, 3.4×105 Pa) for approximately ten minutes, and the reaction mixture was filtered through a layer of CELITE filter agent. The filter cake was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the residue was dried under a stream of nitrogen to provide 3.80 g of 1-tetrahydro-2H-pyran-4-ylacetone as a colorless oil. The vessel was purged with nitrogen, and 10% palladium on carbon (400 mg) was added the reaction mixture was filtered through a layer of CELITE filter agent The filter cake was washed with ethyl acetate The filtrate was concentrated under reduced pressure the residue was dried under a stream of nitrogen

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

Procedure: The method described in Part B of Example 3 was repeated with 1-tetrahydro-4H-pyran-4-ylideneacetone (4.0 g, 28.5 mmol), and the resulting 1-tetrahydro-2H-pyran-4-ylacetone was mixed with diethyl oxalate (4.66 g, 31.9 mmol) and added to a solution of sodium tert-butoxide (3.07 g, 31.9 mmol) in ethanol (22 mL). The reaction was carried out according to the method described in Part C of Example 3 with the following modifications. Hydroxyethylhydrazine (2.43 g, 31.9 mmol) was used instead of ethylhydrazine oxalate. Extractions were carried out seven times with chloroform, and the crude product was not purified. Ethyl 1-(2-hydroxyethyl)-5-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazole-3-carboxylate (8.2 g) was obtained as a viscous yellow oil. Extractions the crude product was not purified

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

Procedure: A solution of 1-tetrahydro-4H-pyran-4-ylideneacetone (4.0 g, 28.5 mmol) in ethyl acetate was added to a Parr vessel. The vessel was purged with nitrogen, and 10% palladium on carbon (400 mg) was added. The vessel was shaken under hydrogen pressure (50 psi, 3.4×105 Pa) for approximately ten minutes, and the reaction mixture was filtered through a layer of CELITE filter agent. The filter cake was washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and the residue was dried under a stream of nitrogen to provide 3.80 g of 1-tetrahydro-2H-pyran-4-ylacetone as a colorless oil. The vessel was purged with nitrogen, and 10% palladium on carbon (400 mg) was added the reaction mixture was filtered through a layer of CELITE filter agent The filter cake was washed with ethyl acetate The filtrate was concentrated under reduced pressure the residue was dried under a stream of nitrogen