1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-[(1R)-1-azidoethyl]-1-benzothiophene

Participants

Reaction Steps

The process was carried out with reference to a method of Thompson, et al. (J. Org. Chem. 1993, 58, 5886). Under an argon atmosphere, a mixture of 5.50 g of (1S)-1-(1-benzothiene-3-yl)ethanol and 7.98 g of DPPA was dissolved in toluene, and 5.54 mL of DBU was then added thereto in an ice bath. After stirring for 30 min under ice-cooling, it was further stirred at room temperature for 15 hours. The reaction mixture was washed with water and 1 M hydrochloric acid in this order, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 5.86 g of (1R)-1-(1-benzothiene-3-yl)ethylazide as a colorless oily substance. EI: 203

Provenance & Evidence