Ammonium Chloride → Methyl 5-(2,6-dimethoxyphenyl)-5-(1,1-dimethylethylsulfinamido)pentanoate

Participants

Reaction Conditions

Reaction Steps

A cooled (−78° C.) yellow solution of commercially available 2-iodo-1,3-dimethoxybenzene (9.930 g; 37.60 mmol) in anh. THF (170 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (23.5 ml; 37.60 mmol). The resulting slightly yellow solution was further stirred at −78° C. for 15 min. A yellow solution of methyl 5-((tert-butylsulfinyl)imino)pentanoate (5.850 g; 25.07 mmol) in anh. THF (12 ml) was then added dropwise to the cooled reaction mixture, and stirring at −78° C. was continued for 45 min. The resulting yellow reaction mixture was treated successively with aq. sat. NH4Cl (80 ml), Et2O (250 ml) and water (75 ml). The separated yellow organic layer was then washed with brine (75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded methyl 5-(2,6-dimethoxyphenyl)-5-(1,1-dimethylethylsulfinamido)pentanoate as a yellow oil. LC-MS (conditions B): tR=0.85 min.; [M+H]+: 372.34 g/mol.

Provenance & Evidence