Réaction #416702

Équation de réaction

water

2-methoxyethoxymethyl chloride

1,5-pentanediol

sodium hydride

→

title compound

Rendement 52.4%

5-(2-Methoxyethoxy)methoxy-1-pentanol

Rendement 52.4%

Solvants

dimethylformamide

dimethylformamide

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Températurewhilst ice-cooling at 5° to 7° C
2. 2
   workup.ADDITIONwere added dropwise, whilst ice-
3. 3
   Températurecooling at 5° to 7° C
4. 4
   workup.STIRRINGThe mixture was stirred at room temperature for 3 hours
5. 5
   Extractionextracted five times with methylene chloride
6. 6
   LavageThe combined extracts were washed with water
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   Concentrationconcentrated by evaporation under reduced pressure

Mode opératoire

A solution of 50.00 g of 1,5-pentanediol dissolved in 100 ml of dimethylformamide was added dropwise to a mixture of 23.00 g of sodium hydride (as a 55% w/w dispersion in mineral oil) in 300 ml of dimethylformamide, whilst ice-cooling at 5° to 7° C. The mixture was stirred at room temperature for 1 hour, after which 65.79 g of 2-methoxyethoxymethyl chloride dissolved in 100 ml of dimethylformamide were added dropwise, whilst ice-cooling at 5° to 7° C. The mixture was stirred at room temperature for 3 hours, after which it was poured into 2.5 liters of water and then extracted five times with methylene chloride. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 850 g of silica gel, and 48.40 g of the title compound were obtained, as a colorless oil, from those fractions eluted with mixtures of methylene chloride and methanol ranging from 98:2 to 95:5 by volume.

Source