Bromide ion → HCID 22413567, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of magnesium turnings (840 mg, 35 g-atom) in THF (25 mL) was activated with iodine crystalls. A few drops of cyclohexylmethyl bromide were added, and the mixture was warmed until the exothermic Grignard reaction commenced. The remaining bromide (4.9 mL; 35 mmol) was added dropowise at a rate sufficient to maintain a gentle reflux. The mixture was refluxed for an additional 30 minutes, cooled to -78° C., and then slowly cannulated to a cold Solution of 4-(4-thiazolylmethoxy)benzaldehyde (7.6 g, 35 mmol), prepared as in step 1, in THF (75 mL), and the resulting solution was allow to stand at ambient temperature for 12 hours. Saturated aqueous NH4Cl (50 mL) was added and the mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified on a silica gel column eluting with 7:3 hexane-ethyl acetate to provide 900 mg of cyclohexylmethyl-(4-(4-thiazolylmethoxy)phenyl) ketone and 5.4 g of 2-cyclohexyl-1-(4-(4-thiazolylmethoxy)phenyl)ethan-1-ol.

Provenance & Evidence