1,2-Dichloroethane → HCID 68062439, compound

Participants

Reaction Steps

To a solution of methanesulphonamide (79.6 mg, 0.837 mmol) and bis[(2,2-dimethylpropanoyl)oxy](phenyl)-lambda-3-iodane (630.0 mg, 1.553 mmol) in isopropyl acetate (6.0 mL) was added 4-[(3,4-dichlorobenzyl)oxy]-2-methoxybenzaldehyde (Preparation 25, 300.0 mg, 0.963 mmol) and 4 Å molecular sieves (500.0 mg). The reaction mixture was stirred for 5 minutes producing a thick suspension. 3,3′-(1,3-Phenylene)bis(2,2-dimethylpropanoic acid)-dirhodium(Rh—Rh) (2:1) (13 mg, 0.017 mmol) was added in one portion and the resulting mixture stirred at room temperature for 10 minutes. 1,2-dichloroethane (5 mL) was then added producing a green solution, which was stirred for further 18 hours under a nitrogen atmosphere at room temperature. The reaction mixture was then concentrated in vacuo and partitioned between DCM and aqueous solution of hydrochloric acid (2 M). The combined organics were dried through a phase separation Cartridge™ and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with 0 to 60% EtOAc in heptane to yield the title compound as pale yellow gum which solidified upon standing (140 mg, 41% yield):

Provenance & Evidence