Sodium hydride → 5-((2-phenoxybenzyloxy)methyl)-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole

A 60% suspension of sodium hydride in mineral oil (4.1 g, 101 mmol) was added to a solution of a mixture of (1-(triphenylmethyl)-4,5,6,7-tetrahydro-1H-benzimidazol-5-yl)-methanol and (3-(triphenylmethyl)-4,5,6,7-tetrahydro-3H-benzimidazol-5-yl)methanol (2.0 g, 5.1 mmol) in THF (8 ml). When the reaction had ceased tetrabutylammonium iodide (0.10 g, 0.25 mmol) and a solution of 2-phenoxybenzyl bromide (1.5 g, 5.6 mmol) in THF (5 ml) were added successively. The reaction mixture was stirred for 16 h. Water (100 ml) was added carefully. The mixture was extracted with ethyl acetate (3×60 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate (100 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (90 g), using ethyl acetate/heptane (gradient from 50:50 to 100:0) as eluent, to give 1.21 g of 5-((2-phenoxybenzyloxy)methyl)-1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole and 5-((2-phenoxybenzyloxy)methyl)-3-triphenylmethyl-4,5,6,7-tetrahydro-3H-benzimidazole.

1. extractionThe mixture was extracted with ethyl acetate (3×60 ml)
2. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogen carbonate (100 ml)
3. dry with materialdried over magnesium sulphate
4. customThe solvent was removed in vacuo
5. customThe crude product was purified by flash chromatography on silica (90 g)

ORD-Eintrag

ord-08500b7de324408a822b2ea0d2de0cfa

Quelldatensatz

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06610721B2