m-Chloroperbenzoic acid → HCID 59215190, compound

Participants

Reaction Steps

To a stirred solution of 2-chloro-5-[2-methyl-3-(methylthio)propyl]-pyridine (2.60 g, 12.5 mmol) in CH2Cl2 (35 mL) cooled to −15° C. in an ice-salt bath was added m-chloroperoxybenzoic acid (mCPBA, ˜85%, 2.54 g, ˜12.5 mmol) portion wise at such a rate that the temperature never rose above −10° C. After the addition was over, TLC showed that a single product plus a small amount of starting material was present in the solution. To avoid any sulfone formation, the reaction was quenched at this point by the addition of saturated NaHCO3 (50 mL). The organic layer was separated and the aqueous phase washed with CH2Cl2 (25 mL). The combined organic layers were dried over MgSO4 and the solvent was evaporated to give 2.66 g of crude product as a yellow oil. The oil was triturated with hot hexane (50 mL) and the hexane decanted after cooling. This procedure removed most of the starting material and the resulting product (a mixture of two diastereomers) was directly used for the following step without further purification. [M+H]+=232, 234; δ 1.09 (overlapping d, 3H), 2.57, 2.59 (2 s, 3H).

Provenance & Evidence