Hydrochloric Acid → HCID 11694086, compound

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Reaction Steps

A stirring bar and Mg (1.2 g) were placed in a 500 ml-capacity three neck flask, and the flask was connected to a condenser and sufficiently dried. Then, a nitrogen atmosphere was established in the flask, and THF (20 ml) and I2 were added thereto. 1-bromo-5-hexene (7) (8 g, 5 mmol) and THF (10 ml) were added to the brown suspension thus obtained to start a reaction, and heat developed when a color of I2 disappeared. Immediately after the start of the heat development, the flask was placed in an ice bath. Then, after generation of a Grignard reagent, HCOOMe (1.5 ml, 5 mmol) was slowly dropped into the flask, and the mixture thus obtained was stirred for 30 minutes. When generation of alcohol was recognized by thin-layer chromatography, diluted hydrochloric acid was added to the mixture to stop the reaction. An organic layer was extracted with AcOEt and dried over Na2SO4, and the solvent was distilled off under reduced pressure. Thereafter, the organic layer was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1), (hexane:ethyl acetate=4:1). Thus, intended 1,12-tridecadiene-7-ol (8) (2.55 g, 1.3 mmol, yield: 26%) was obtained. 1HNMR values of 1,12-tridecadiene-7-ol (8) are shown below.

Provenance & Evidence