Ethanol → 3-(7-Chloroquinol-2-ylmethoxy)benzyl alcohol

反応式

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH:17]=[O:18])=[N:9]2)=[CH:4][CH:3]=1.CCO.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:17][OH:18])[CH:19]=[CH:20][CH:21]=3)=[N:9]2)=[CH:4][CH:3]=1

参加物

実験手順

The aldehyde of Step 1 (46.64 g, 156.6 mmol) was dissolved in 300 mL of THF. At 0° C., 800 mL of EtOH was added, followed by NaBH4 (5.93 g, 157 mmol). The mixture was then stirred at r.t. (room temperature) for 1 h and poured into cold 25% aq (aqueous) NH4OAc. The organic solvents were evaporated and the title alcohol was extracted with toluene:THF 1:1, dried over Na2SO4 and filtered through silica to yield 47.9 g of the title compound.