Dimethylformamide → 5-(Benzyloxy)pentan-1-ol

Participants

Reaction Conditions

Reaction Steps

31.5 g of sodium hydride (60% strength) are ire educed into 900 ml of abs. DMF in portions at room temperature. 104.8 ml of 1,5-pentanediol in 450 ml of abs. DMF are added dropwise to the suspension cooled to −20° C., such that the internal temperature does not exceed −15° C. After addition is complete, a solution of 121 ml of benzyl bromide in 870 ml of abs. DMF is rapidly added dropwise and the reaction mixture is then stirred at room temperature for 30 minutes. The reaction is ended by careful addition of 315 ml of water. For work-up, the reaction mixture is stirred into 1.5 l of water and extracted 3 times with 1 l of ether in each case. The ethereal phases are combined, washed with water, dried over magnesium sulphate and concentrated in vacuo. Chromatography on silica gel using a hexane-ethyl acetate gradient yields 85 g of 5-benzyloxypentan-1-ol as an oil.

Provenance & Evidence