Sodium borohydride → 4-(6-Carbomethoxyhexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazole

Participants

Reaction Steps

The solution of 143 mg of sodium borohydride in 30 ml of water was added to the solution of 2.65 g of 4-(6-carbomethoxyhexyl)-5-(3-keto-1-trans-octenyl)-thiazole (Ia, R1 = H) in 30 ml of isopropanol. The obtained reaction mixture was stirred for 2 hours at room temperature, then poured onto 150 ml of water, and extracted with 3 × 75 ml of ethyl acetate. The ethyl acetate extract was washed with water to neutral and evaporated in vacuo. The obtained 2.5 g of evaporation residue was subjected to chromatography on a column prepared with 100 g of silicic acid, the elution was carried out with mixtures of n-heptane and ethyl acetate of gradually increasing ethyl acetate content. The desired 4-(6-carbomethoxyhexyl)-5-(3-hydroxy-1-trans-octenyl-thiazole, (Ic, R1 = H) was eluted from the column with a mixture consisting of 70 % n-heptane and 30 % ethyl acetate, affording 2.2 g of a product of chromatographic purity.

Provenance & Evidence