Acetone → (4-Ethoxy-3-methanesulfonyl-quinolin-6-yl)-methanol

Participants

Reaction Steps

A solution of 4-ethoxy-3-methanesulfonyl-quinoline-6-carboxylic acid ethyl ester (example 74a) in anhydrous dichloromethane (500 mL) was cooled to −78 degrees by acetone and dry-ice bath. DIBAL-H in toluene (1M, 50.8 mL, 50.8 m mol) was added dropwise into the above solution. The solution was allowed to react at −78 degrees for 4 hours. Then methanol was added to the reaction mixture. The resulted reaction mixture was stirred at −78 degrees for another 30 min, and then warmed to room temperature slowly. After the reaction, the solvent was evaporated; dichloromethane was added to the residue. After filtering out the insoluble, filtrate was collected, and concentrated to give (4-ethoxy-3-methanesulfonyl-quinolin-6-yl)-methanol which was used in the next step reaction without further purification. LC-MS m/e 282 (MH+).

Provenance & Evidence