Reacción #1014

Ecuación de reacción

Caesium carbonate

3-hydroxy-4-methoxybenzaldehyde

cyclopentyl bromide

cyclopentyl bromide

caesium carbonate

→

title compound

Rendimiento 89.4%

3--Cyclopentyloxy-4-methoxybenzaldehyde

Rendimiento 89.4%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter a further 6 h at RT
2. 2
   Filtraciónthe mixture was filtered
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (300 ml)
5. 5
   Lavadowashed with sodium hydroxide solution (10%; 2×150 ml)
6. 6
   SecadoThe organic layer was dried (MgSO4)
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   workup.DISTILLATIONdistilled (150° C., 10-2 mbar)

Procedimiento

Caesium carbonate (214 g, 0.66 mol) was added to a mixture of 3-hydroxy-4-methoxybenzaldehyde (100 g, 0.66 mol) and cyclopentyl bromide (98 g, 0.66 mol) in anhydrous DMF (50 ml). The reaction mixture was stirred at RT for 16 h then treated with a further portion of cyclopentyl bromide (98 g, 0.66 mol) and caesium carbonate (214 g, 0.66 mol). After a further 6 h at RT, the mixture was filtered and concentrated in vacuo. The residue was dissolved in dichloromethane (300 ml) and washed with sodium hydroxide solution (10%; 2×150 ml). The organic layer was dried (MgSO4), concentrated in vacuo, and distilled (150° C., 10-2 mbar) to afford the title compound (130 g) as a viscous colourless oil. (Found: C, 70.38; H, 7.48. C13H16O3 requires C, 70.89; H 7.32%); δH (CDCl3) 1.5-2.0 (8H, br m, CH2)4), 3.87 (3H, s, OMe), 4.80 (1H, br m, OCHCH2), 6.90 (1H, d, J 8.7 Hz. ArH ortho to OMe), 7.30-7.45 (2H, m. 2×ArH meta to OMe), and 9.77 (1 H, s, ArCHO).

Fuente