Benzyl Alcohol → Benzyl azide

Participants

Reaction Steps

2.07 ml of benzyl alcohol (20 mmole), 2.99 g of DMAP (1.2 eq) and 1.86 ml of MeSOCl2 (1.2 eq) were sequentially added to 25 ml of DMF. After stirring the mixture for 6 hours, 3.96 g of NaN3 (3 eq) was added thereto, and the mixture was stirred for 12 hours. The reaction mixture was treated with a mixture of diethyl ether and water, the ether extract was dried under MgSO4, ether was removed under a reduced pressure, and the resulting residue was subjected to column chromatography (silica gel 60, 230˜400 meshes, Merck) to obtain the title compound as a pale yellow liquid. The chromatography was conducted using a mixture of hexane and CH2Cl2 as an eluting solution whose mix ratio was gradually varied from 2:1 to 1:1 (v/v).

Provenance & Evidence