Réaction #82216

Équation de réaction

lithium aluminum hydride

ethyl 2-(4-morpholinyl)thiazole-4-carboxylate

→

desired compound

Rendement 61.1%

2-(4-Morpholinyl)-4-(hydroxymethyl)thiazole

Rendement 61.1%

Solvants

toluene

THF

THF

Conditions de réaction

Traitement

1. 1
   Autrequenched cautiously with aqueous Rochelle's salts
2. 2
   workup.ADDITIONdiluted with chloroform
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated in vacuo

Mode opératoire

A solution of 7.0 ml (7.0 mmol) of lithium aluminum hydride in toluene was diluted with 10 ml of THF, cooled to 0° C., and treated with a solution of 1.7 g (7.0 mmol) of ethyl 2-(4-morpholinyl)thiazole-4-carboxylate in 25 ml of THF. The resulting solution was stirred for 1 h, quenched cautiously with aqueous Rochelle's salts, diluted with chloroform, filtered, dired over Na2SO4, and concentrated in vacuo. Silica gel chromatography using 2-4% methanol in chloroform provided 856 mg (61%) of the desired compound, Rf 0.16 (4% methanol in chloroform). 1H NMR (CDCl3) δ 2.44 (br, 1 H), 3.46 (t, J=5 Hz, 4 H), 3.81 (t, J=5 Hz, 1 H), 4.55 (br s, 2 H), 6.45 (s, 1 H). Mass spectrum: (M+H)+ =200.

Source