反应 #554661

反应方程式

DIAD

(1-benzyl-7-methylazepan-3-yl)methanol

4-fluoro-3-methylphenol

triphenyl phosphine resin

→

6-[(4-fluoro-3-methylphenoxy)methyl]-1-benzyl-2-methylazepane

溶剂

dichloromethane

反应条件

后处理

1. 1
   过滤The mixture was filtered
2. 2
   浓缩filtrate was concentrated
3. 3
   其他The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes gradient)

实验过程

A mixture of (1-benzyl-7-methylazepan-3-yl)methanol (2-5, 500 mg, 2.1 mmol, 1.0 equiv), 4-fluoro-3-methylphenol (300 mg, 2.4 mmol, 1.1 equiv), and PS-triphenyl phosphine resin (1.2 g, 2.4 mmol, 1.1 equiv) in dichloromethane (25 mL) was treated with DIAD (0.46 mL, 480 mg, 2.4 mmol, 1.1 equiv) and the resulting suspension was stirred for 16 hours at 23° C. The mixture was filtered and filtrate was concentrated. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes gradient) to yield 6-[(4-fluoro-3-methylphenoxy)methyl]-1-benzyl-2-methylazepane (2-6) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.37 (m, 5H), 6.86 (m, 1H), 6.55 (m, 2H), 3.72-1.75 (m, 20H). LRMS m/z (M+H) 342.3 found, 242.2 required.

来源