Réaction #11294

Équation de réaction

ether

methoxyethoxymethyl chloride

4-iodophenol

sodium hydride

→

4-Methoxyethoxymethoxy-iodobenzene

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurewarmed to room temperature
2. 2
   workup.STIRRINGstirred for 24 hours
3. 3
   AutreThe solvent was removed under reduced pressure
4. 4
   Lavagewashed with 5% sodium hydroxide (4×200 ml), water (4×200 ml), saturated sodium chloride (1×200 ml)
5. 5
   Séchagedried over sodium sulfate
6. 6
   AutreEvaporation of the solvent under reduced pressure
7. 7
   Autregave an oily product in 14.1 g

Mode opératoire

A solution of 4-iodophenol (10 g, 45.45 mmol) in 200 ml of anhydrous tetrahydrofuran was treated at 0° C. with sodium hydride (2.36 g, 60% dispersion, 59.09 mmol) for 5 minutes. To the resulting mixture, methoxyethoxymethyl chloride (8.3 ml, 72.73 mmol) was slowly added over a 5-minute period. The mixture was stirred at 0° C. under nitrogen for 30 minutes, warmed to room temperature, and stirred for 24 hours. The solvent was removed under reduced pressure. The residue was taken into 500 ml of ether, washed with 5% sodium hydroxide (4×200 ml), water (4×200 ml), saturated sodium chloride (1×200 ml), and dried over sodium sulfate. Evaporation of the solvent under reduced pressure gave an oily product in 14.1 g. TLC (silica gel, ether): Rf 0.5.

Source