p-Toluenesulfonic acid → HCID 22633460、化合物

反応式

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:16][CH2:17][CH3:18])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=CC=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22](S(O)(=O)=O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C[N:37]([CH:39]=[O:40])C>>[CH2:29]([O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][CH2:2][C:7]2[N:37]=[C:39]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:40][C:6]=2[CH3:5])=[CH:10][C:11]=1[CH2:16][CH2:17][CH3:18])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

反応物 4

HCID 6101p-Toluenesulfonic acid

HCID 6228Dimethylformamide

HCID 10796Cesium carbonate

HCID 222611274-Benzyloxy-2-propylphenol

生成物 1

HCID 22633460HCID 22633460、化合物

反応条件

温度: 55 °C

実験手順

A mixture of 4-benzyloxy-2-propylphenol (3.89 mmol), toluene-4-sulfonic acid 2-(5-methyl-2-biphenyl-4-yl-oxazol-4-ly) ethyl ester (4.67 mmol) (see Ex. 1, part F) and cesium carbonate (1.65 g 5.06 mmol) in anhydrous DMF (8 mL) was heated for 18 h at 55° C. The mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate (100 mL) and water (50 mL), washed with brine (50 mL), dried (Na2SO4), and removed in vacuo to give a crude oil which was purified using the Biotage FlashElute chromatography system using a 40 L normal phase cartridge, eluting with 10-15% ethyl acetate/hexanes to give 4-[2-(4-benzyloxy-3-propylphenoxy)ethyl]-5-methyl-2-phenyloxazole.