Azobisisobutyronitrile → HCID 14820509、化合物

反応式

[OH:1][C:2]1[C:3]([CH2:11][CH:12]=[CH2:13])=[CH:4][C:5]2[S:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.CC(N=NC(C#N)(C)C)(C#N)C.[C:26]1([SH:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(=O)(O)[O-].[Na+]>[OH:1][C:2]1[C:3]([CH2:11][CH2:12][CH2:13][S:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:4][C:5]2[S:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

参加物

反応条件

温度: 90 °C

実験手順

To a solution of 5-hydroxy-6-allyl-2,3-dihydrobenzothiophene (125 mg, 0.65 mmole) in 0.5 mL thiophenol was added 28 mg AIBN. The reaction mixture was purged with nitrogen and heated to 90° C. for 3 hours. TLC analysis (90/10 hexane/EtOAc) showed the reaction to be complete. The reaction mixture was diluted with 25 mL saturated sodium bicarbonate and extracted 3×25 mL EtOAc. The combined organics were washed with sodium bicarbonate (2×25 mL), H2O (1×25 mL) and brine (1×25 mL). Drying over Na2SO4, filtration and concentration afforded 568 mg crude product as an oil. Purification by flash chromatography (90/10, hexane/EtOAc) 126 mg (64%) pure product NMR 287 MS181.