2-Bromopropene → HCID 534462, compound

Participants

Reaction Steps

2-Propenyl magnesium bromide is prepared under nitrogen from 2-bromopropene (50 g, 0.417 M) and magnesium (12 g, 0.5 M) in tetrahydrofuran (150 ml) in the usual manner. To this reagent, a solution of 4-methylene-5-hexenal (62 g, 0.564 M) in tetrahydrofuran (100 ml) is slowly added during a two hour period at 0° C. After the addition is complete, the mixture is allowed to warm to room temperature and then stirred overnight. The resulting mixture is poured into cold saturated ammonium chloride solution (500 ml) and the aqueous layer is extracted with ether (3×500 ml). The combined organic layers are dried (Na2SO4) and the solvent is removed in vacuo. The residue (56.5 g) is purified by column chromatography on silica gel (350 g) with 25% ether in petroleum ether to give 2-methyl-6-methylene-1,7-octadien-3-ol (32 g, 51%) as a colorless liquid.

Provenance & Evidence