Réaction #55607

Équation de réaction

2-chloro-α,α,α-trifluoro-p-tolyl-3-(1-carbethoxyethoxy)-4-nitrophenyl ether

lithium aluminum hydride

→

2-chloro-α,α,α-trifluoro-p-tolyl-3-(1-hydroxymethylethoxy)-4-nitrophenyl ether

Solvants

ether

ether

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONadded
2. 2
   TempératureThe temperature increases to about 0° to 10° C.
3. 3
   Autreafter a total of 45 seconds, the reaction mixture is quenched
4. 4
   workup.ADDITIONby pouring
5. 5
   workup.STIRRINGwith stirring, onto ice/dilute sulfuric acid
6. 6
   LavageThe ether phase is washed with water
7. 7
   Autredried
8. 8
   Filtrationfiltered through activated silica gel
9. 9
   Autrethe solvent removed

Mode opératoire

A solution of 2-chloro-α,α,α-trifluoro-p-tolyl-3-(1-carbethoxyethoxy)-4-nitrophenyl ether (17.32 g, 0.04 mole) in dry ether (500 ml) is treated at -10° C. with a suspension of lithium aluminum hydride (1.9 g) in ether (approximately 100 ml) added with stirring over ten seconds. The temperature increases to about 0° to 10° C. and after a total of 45 seconds, the reaction mixture is quenched by pouring, with stirring, onto ice/dilute sulfuric acid. The ether phase is washed with water, dried, filtered through activated silica gel, and the solvent removed to give 2-chloro-α,α,α-trifluoro-p-tolyl-3-(1-hydroxymethylethoxy)-4-nitrophenyl ether as a dark oil, yield 14 g.

Source