Benzyl Alcohol → HCID 89714609, compound

Participants

Reaction Conditions

Reaction Steps

6.20 ml of benzyl alcohol (59.64 mmol) are placed in 400 ml of anhydrous THF. The solution is cooled to 4° C. in an ice bath and 2.39 g of 60% sodium hydride (59.64 mmol) are added portionwise. The reaction mixture is stirred at 4° C. for 15 minutes. 15 g of 4-chloro-6-ethyl-8,8-dimethyl-2-methylsulfanyl-7,8-dihydro-6H-9-oxa-1,3,6-triazabenzo cyclohepten-5-one (49.70 mmol) dissolved in 400 ml of anhydrous THF are added dropwise. After stirring for 2 hours at 4° C., 400 ml of water are added and the THF is evaporated off. The aqueous phase is extracted twice with 300 ml of DCM, and the organic phases are combined and washed with 400 ml of water and then 400 ml of brine. The organic phase is dried over Na2SO4, filtered and concentrated. The residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 30% to 50%. 18.6 g of 4-benzyloxy-6-ethyl-8,8-dimethyl-2-methylsulfanyl-7,8-dihydro-6H-9-oxa-1,3,6-triazabenzocyclohepten-5-one are obtained.

Provenance & Evidence