반응 #6705

반응 방정식

ether

methoxyethoxymethyl chloride

4-iodophenol

sodium hydride

→

4-Methoxyethoxymethoxy-iodobenzene

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도warmed to room temperature
2. 2
   workup.STIRRINGstirred under nitrogen for 24 hours
3. 3
   기타The solvent was removed
4. 4
   세척washed with 200 ml of 5% sodium hydroxide (4×200 ml), water (4×200 ml), saturated sodium chloride (1×200 ml)
5. 5
   건조dried over sodium sulfate
6. 6
   기타Evaporation of the solvent under reduced pressure
7. 7
   기타gave an oily product in 14.1 g

실험 절차

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 was slowly added over a 5-minute period methoxyethoxymethyl chloride (8.3 ml, 72.73 mmol). The mixture was stirred at 0° C. for 30 minutes, warmed to room temperature, and stirred under nitrogen for 24 hours. The solvent was removed under reduce pressure. The residue was taken into 500 ml of ether, washed with 200 ml of 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.

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