Pentadecane-7,9-dione

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

Procedure: Pentadecane-7,9-dione (60.0 g, 250 mmol) and 30 g (500 mmol) of urea were dissolved in 3750 mL of ethanol, and under a nitrogen atmosphere, 75 mL of concentrated hydrochloric acid was added, and the mixture was gradually heated until reflux, and allowed to reflux for 18.5 hours. After cooling down to room temperature, water and ethyl acetate were added, the oil phase was extracted, and washed with a saturated sodium bicarbonate solution and saturated saline in this order, and dried over magnesium sulfate and concentrated. The resultant concentrate was purified by a silica gel column (hexane•ethyl acetate) to obtain 31.2 g of 4,6-dihexylpyrimidin-2-ol. the mixture was gradually heated until reflux to reflux for 18.5 hours the oil phase was extracted washed with a saturated sodium bicarbonate solution and saturated saline in this order dried over magnesium sulfate concentrated The resultant concentrate was purified by a silica gel column (hexane•ethyl acetate)

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

Procedure: Pentadecane-7,9-dione (60.0 g, 250 mmol) and 30 g (500 mmol) of urea were dissolved in 3750 mL of ethanol, and under a nitrogen atmosphere, 75 mL of concentrated hydrochloric acid was added, and the mixture was gradually heated until reflux, and allowed to reflux for 18.5 hours. After cooling down to room temperature, water and ethyl acetate were added, the oil phase was extracted, and washed with a saturated sodium bicarbonate solution and saturated saline in this order, and dried over magnesium sulfate and concentrated. The resultant concentrate was purified by a silica gel column (hexane•ethyl acetate) to obtain 31.2 g of 4,6-dihexylpyrimidin-2-ol. the mixture was gradually heated until reflux to reflux for 18.5 hours the oil phase was extracted washed with a saturated sodium bicarbonate solution and saturated saline in this order dried over magnesium sulfate concentrated The resultant concentrate was purified by a silica gel column (hexane•ethyl acetate)

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

Procedure: Lithium amide (12.4 g, 498 mmol) was dissolved in 130 mL of methyl t-butyl ether (MTBE), and a solution of 32.4 g (253 mmol) of octan-2-one in MTBE (67 mL) was dropped under a nitrogen atmosphere at 35° C. and the mixture was stirred for 1 hour. Then, into this was dropped a solution of 80.0 g (506 mmol) of ethyl pentanoate in MTBE (67 mL), and the mixture was stirred at 35° C. for 4.5 hours. After cooling, the resultant mixed liquid was added into concentrated hydrochloric acid containing ice added, and the oil phase was extracted and died over sodium sulfate, then, concentrated. For purification of the resultant concentrate, a copper acetate aqueous solution was added to cause crystallization of a copper complex of the concentrate, which was dissolved in MTBE and mixed with a sulfuric acid aqueous solution and the mixture was returned to the concentrate, and the oil phase was extracted and dried over sodium sulfate and concentrated, to obtain 36.3 g (151 mmol) of pentadecane-7,9-dione. the mixture was stirred at 35° C. for 4.5 hours After cooling the resultant mixed liquid containing ice added the oil phase was extracted concentrated For purification of the resultant concentrate a copper acetate aqueous solution was added crystallization of a copper complex of the concentrate, which was dissolved in MTBE mixed with a sulfuric acid aqueous solution the oil phase was extracted dried over sodium sulfate concentrated

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

Procedure: Lithium amide (12.4 g, 498 mmol) was dissolved in 130 mL of methyl t-butyl ether (MTBE), and a solution of 32.4 g (253 mmol) of octan-2-one in MTBE (67 mL) was dropped under a nitrogen atmosphere at 35° C. and the mixture was stirred for 1 hour. Then, into this was dropped a solution of 80.0 g (506 mmol) of ethyl pentanoate in MTBE (67 mL), and the mixture was stirred at 35° C. for 4.5 hours. After cooling, the resultant mixed liquid was added into concentrated hydrochloric acid containing ice added, and the oil phase was extracted and died over sodium sulfate, then, concentrated. For purification of the resultant concentrate, a copper acetate aqueous solution was added to cause crystallization of a copper complex of the concentrate, which was dissolved in MTBE and mixed with a sulfuric acid aqueous solution and the mixture was returned to the concentrate, and the oil phase was extracted and dried over sodium sulfate and concentrated, to obtain 36.3 g (151 mmol) of pentadecane-7,9-dione. the mixture was stirred at 35° C. for 4.5 hours After cooling the resultant mixed liquid containing ice added the oil phase was extracted concentrated For purification of the resultant concentrate a copper acetate aqueous solution was added crystallization of a copper complex of the concentrate, which was dissolved in MTBE mixed with a sulfuric acid aqueous solution the oil phase was extracted dried over sodium sulfate concentrated