Pentanoic Acid → HCID 18647421, compound

Participants

Reaction Steps

A solution of (S)-2-tetrahydropyranyloxy-1-(p-toluenesulfonyloxy)-propane (192 g, 0.62 mol) prepared in the same manner as in a process described in Example 1 of the specification of Japanese patent application No. Sho 61-133269/1986 in tetrahydrofuran (hereinafter abbreviated to THF) (2,000 ml) was added to a mixture of 60% sodium hydride (31 g, 0.62 mol), 5-hydroxy-2-(4'-propyl-4"-biphenylyl)pyrimidine (150 g, 0.52 mol) and THF (1,200 ml), followed by agitating the resulting mixture at 60° C. for 4 hours, allowing it to cool down to room temperature, adding toluene, washing the resulting organic layer with an alkali and then with water, concentrating it, dissolving the concentrate in ethanol (2,000 ml), adding 6N-hydrochloric acid (40 ml), agitating the mixture at 60° C. for one hour, allowing it to cool down to room temperature, collecting deposited crystals and recrystallizing them from ethyl acetate (1,000 ml) to obtain (S)-5-(2'-hydroxypropyloxy)-2-(4'-propyl-biphenyl-4-yl)-pyrimidine (122 g), which was a liquid crystal and had phase transition points of C-Ch point 161.0° C. and Ch-I point 208.1° C. This (S)-5-(2'-hydroxypropoxy)-2-(4'-propyl-biphenyl-4-yl)pyrimidine (10 g, 0.029 mol), n-pentanoic acid (4.4 g, 0.044 mol), dicyclohexylcarbodiimide (hereinafter abbreviated to DCC) (24 g, 0.12 mol) and dimethylaminopyridine (hereinafter abbreviated to DMAP) (3.9 g) were dissolved in dichloromethane (150 ml), followed by agitating the solution at room temperature for 2 hours, filtering off deposited crystals, washing the filtrate with an alkali and then with water, concentrating it and twice recrystallizing the residue from ethanol (200 ml) to obtain (S)-5-(2'-valeryloxypropoxy)-2-(4'-propyl-biphenyl-4-yl)-pyrimidine (9.8 g).

Provenance & Evidence