2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl 7-(N-(4-(1-hydroxyhexyl)phenyl)acetamido)hept-5-ynoate

Participants

Reaction Conditions

Reaction Steps

4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile (19 mg, 0.081 mmol) was added to a solution of the MPM-ether 104 (35 mg, 0.071 mmol) in CHCl3 (1.6 mL) and H2O (0.1 mL) at 0° C. After stirring for 2 h at 0° C. the reaction was quenched with sodium bicarbonate and extracted with EtOAc. The organic portion was washed with saturated aqueous sodium hydrogen sulfate and brine, then dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 3:2 hex/EtOAc) to yield 23 mg (87%) of the hydroxyl-ester 105.

Provenance & Evidence