Réaction #554661

Équation de réaction

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

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   FiltrationThe mixture was filtered
2. 2
   Concentrationfiltrate was concentrated
3. 3
   AutreThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes gradient)

Mode opératoire

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.

Source