Reacción #2286322

Ecuación de reacción

sodium chloride

acetonitrile

(2,6-Dibromo-4-hydroxymethyl-phenyl)-acetonitrile

3,4-dihydro-2H-pyran

sodium bicarbonate

→

[2,6-dibromo-4-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-acetonitrile

Rendimiento 85.4%

[2,6-Dibromo-4-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-acetonitrile

Rendimiento 85.4%

Disolventes

methylene chloride

water

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThis mixture was extracted with methylene chloride (3×50 mL)
2. 2
   Lavadowashed with a saturated aqueous sodium chloride solution (30 mL)
3. 3
   Secadodried with magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated under vacuum
6. 6
   OtroThe resulting oil was purified by flash chromatography (Isco 120 g column)
7. 7
   Lavadoeluted with 15% ethyl acetate in hexanes
8. 8
   OtroThe desired fractions were collected
9. 9
   Concentraciónconcentrated under vacuum
10. 10
    Otroto afford an oil which
11. 11
    Otrowas dried under high vacuum

Procedimiento

A solution of 2,6-dibromo-4-hydroxymethyl-phenyl)-acetonitrile (59) (1.4 g, 4.59 mmol) in methylene chloride (30 mL) at room temperature was treated with 3,4-dihydro-2H-pyran (0.46 mL, 5.04 mmol) and p-toluenesulfonic acid monohydrate (16.10 mg, 0.085 mmol). The reaction mixture was stirred for 45 min and was then treated with a saturated aqueous sodium bicarbonate solution (3 mL), a saturated aqueous sodium chloride solution (10 mL) and water (10 mL). This mixture was extracted with methylene chloride (3×50 mL). The organic layers were combined and washed with a saturated aqueous sodium chloride solution (30 mL), dried with magnesium sulfate, filtered and concentrated under vacuum. The resulting oil was purified by flash chromatography (Isco 120 g column) using silica gel eluted with 15% ethyl acetate in hexanes. The desired fractions were collected and concentrated under vacuum to afford an oil which was dried under high vacuum to afford of [2,6-dibromo-4-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-acetonitrile (60) as a pale yellow oil (1.52 g, 85.4%). Used without further purification. Molecular Weight=389.0892; Exact Mass=386.9470

Fuente