Sodium Azide → 2-Azidomethyl-3-phenylbenzo[b]thiophene

反応式

[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]1([C:11]2[C:12]3[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=3[S:14][C:15]=2[CH2:16]OS(C)(=O)=O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CN(C=O)C.O>[N:1]([CH2:16][C:15]1[S:14][C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=2[C:11]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[N+:2]=[N-:3]

参加物

実験手順

Sodium azide (179 mg, 2.76 mmol) was added to a solution of methanesulfonic acid 3-phenylbenzo[b]thiophen-2-ylmethyl ester (828 mg, 1.84 mmol) in DMF (10 mL) and the mixture stirred at RT for 18 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic fraction was washed with brine, dried (Na2SO4) and concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-35% DCM in cyclohexane) affording the title compound as a clear oil (244 mg, 50%). LCMS (Method C): RT 4.46 min [M+H-N2]+ 237.8