Sodium Methoxide → HCID 54474138, compound

Participants

Reaction Steps

A mixture of 23 g of (S)-2-(methoxymethylidene)-7-methylnonanal, 26.2 g of 4-isopropoxybenzamidine hydrochloride and 250 ml of absolute methanol was treated dropwise at 10° C. with 80 ml of a 5% solution of sodium methylate in methanol. The reaction mixture was stirred at room temperature overnight and subsequently made acid (pH 4-5) with concentrated hydrochloric acid, filtered and the filtrate was concentrated. The residue was taken up in 500 ml of dichloromethane, washed several times with water, dried over sodium sulphate and concentrated. Chromatography of the residue on silica gel with hexanethyl acetate (vol. 19:1) and recrystallization from methanol gave 22.2 g of (S)-2-(4-isopropoxyphenyl)-5-(5-methylheptyl)pyrimidine; m.p. 47.2°-47.7° C.

Provenance & Evidence