hexadecanal

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

Procedure: TZD16 was prepared according to General Procedure A presented hereinabove using 2,4-thiazolidinedione and palmitaldehyde as reactants. TZD16 was prepared

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

Procedure: TZD16 was prepared according to General Procedure A presented hereinabove using 2,4-thiazolidinedione and palmitaldehyde as reactants. TZD16 was prepared

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

Procedure: The reaction of hexadecanal (1.2 g) and tertbutyl bromoacetate (1.56 g) was carried out under the presence of activated zinc (0.59 g) according to similar manner to that of Preparation 1-(1) to afford an oil of tert-butyl 3-hydroxyoctadecanoate. of Preparation 1-(1)

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

Procedure: A solution comprising 10 g (85 mmole) of 1-hexadecanol in 100 ml of methylene chloride was added to a mixture comprising 10 g (139 mmole) of pyridinium chlorochromate, 30 g of celite and 12.0 g (146 mmole) of anhydrous sodium acetate in 400 ml of methylene chloride in a dropwise fashion. Following addition, the reaction mixture was stirred at room temperature for three hours then 300 ml of diethyl ether was added. The reaction mixture was filtered and a precipitate was collected and washed with diethyl ether until clear. The solvent was removed under reduced pressure and the residue passed through Florisil with diethyl ether as the eluent. The solvent was removed under reduced pressure and the residue purified by flash chromatography on silica (230 to 400 mesh) with hexanes and ethyl acetate at a ratio of approximately 39 to 1. The synthesis yielded hexadecanal having a mass of approximately 17.5 g and of approximately 88.4% purity. Hexadecanal is a white wax having a melting point of approximately 33°-34 C. The 1H NMR spectrum of the compound at 300 MHz using CDCl3 comprised the following peaks: δ 0.892 (3H, t, J=6.5Hz), 1.267 (24H, bs), 1.61 to 1.66 (2H, m), 2.430 (2H, dt, J=1.7 and 7.3 Hz), and 9.776 (1H, s). addition The reaction mixture was filtered a precipitate was collected washed with diethyl ether until clear The solvent was removed under reduced pressure The solvent was removed under reduced pressure the residue purified by flash chromatography on silica (230 to 400 mesh) with hexanes and ethyl acetate at a ratio of approximately 39 to 1

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

Procedure: A solution comprising 10 g (85 mmole) of 1-hexadecanol in 100 ml of methylene chloride was added to a mixture comprising 10 g (139 mmole) of pyridinium chlorochromate, 30 g of celite and 12.0 g (146 mmole) of anhydrous sodium acetate in 400 ml of methylene chloride in a dropwise fashion. Following addition, the reaction mixture was stirred at room temperature for three hours then 300 ml of diethyl ether was added. The reaction mixture was filtered and a precipitate was collected and washed with diethyl ether until clear. The solvent was removed under reduced pressure and the residue passed through Florisil with diethyl ether as the eluent. The solvent was removed under reduced pressure and the residue purified by flash chromatography on silica (230 to 400 mesh) with hexanes and ethyl acetate at a ratio of approximately 39 to 1. The synthesis yielded hexadecanal having a mass of approximately 17.5 g and of approximately 88.4% purity. Hexadecanal is a white wax having a melting point of approximately 33°-34 C. The 1H NMR spectrum of the compound at 300 MHz using CDCl3 comprised the following peaks: δ 0.892 (3H, t, J=6.5Hz), 1.267 (24H, bs), 1.61 to 1.66 (2H, m), 2.430 (2H, dt, J=1.7 and 7.3 Hz), and 9.776 (1H, s). addition The reaction mixture was filtered a precipitate was collected washed with diethyl ether until clear The solvent was removed under reduced pressure The solvent was removed under reduced pressure the residue purified by flash chromatography on silica (230 to 400 mesh) with hexanes and ethyl acetate at a ratio of approximately 39 to 1

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

Procedure: 21.5 g (100 mmol) of pyridinium chlorochromate are suspended in 200 ml of anhydrous dichloromethane. 16 g (66 mmol) of hexadecanol in 50 ml of anhydrous dichloromethane are added dropwise. After 2 hours, the mixture is diluted with 300 ml of anhydrous ether, and the solution is decanted off from the black residue. The residue is washed three times with about 50 ml of anhydrous ether. The organic phases are combined and the ether is evaporated off to dryness. The residue is chromatographed on silica gel using petroleum ether/ethyl acetate 9:1. Yield: 15 g (95%), melting point 33°-34° C. the solution is decanted off from the black residue The residue is washed three times with about 50 ml of anhydrous ether the ether is evaporated off to dryness The residue is chromatographed on silica gel

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

Procedure: TZD16 was prepared according to General Procedure A presented hereinabove using 2,4-thiazolidinedione and palmitaldehyde as reactants. TZD16 was prepared