1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(1-Azidoethyl)-5-methylthiophene

Participants

Reaction Steps

Add DBU (1.228 g, 1.2 mL, 8.07 mmol) to a solution of (−)-2-(1-hydroxyethyl)-5-methylthiophene (0.955 g, 6.72 mmol) and diphenylphosphoryl azide (2.22 g, 1.74 mL, 8.07 mmol) in anhydrous toluene. Stir at room temperature for 18 h. Dilute the mixture with EtOAc and wash with water and 0.5N aqueous HCl. Dry the organic phase over Na2SO4, filter and concentrate. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 19:1) to obtain the desired intermediate as an oil (0.875 g, 78%). GC-MS m/z 167 (M+).

Provenance & Evidence