Iodine → HCID 59568794, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of Mg turnings (134.0 mg, 5.6 mg-at.) and catalytic amount of iodine in 20 mL THF was added dropwise 2-(2-bromoethyl)-[1,3]dioxolane (500.0 mg, 2.8 mmol) with heating over a period of 30 min. After stirring the mixture for 30 min at 63° C. the reaction was cooled to −30° C. and 2-methyl-benzaldehyde (275.0 mg, 2.5 mmol) was slowly added as a solution in 5 mL THF. The temperature was maintained at −30° C. for 1 h and then slowly raised to room temperature over a period of 3 h. The excess Grignard reagent was destroyed by the careful addition of saturated aqueous NH4Cl (40 mL). The resulting mixture was extracted with ethyl acetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL). After evaporation of the solvent, the product was isolated by flash column chromatography eluting with 0 to 50% EtOAc/hexanes affording 290 mg of the title compound as a light yellow oil.

Provenance & Evidence