Ethyl 2-(morpholin-4-yl)-1,3-thiazole-4-carboxylate → [2-(Morpholin-4-yl)-1,3-thiazol-4-yl]methanol

HRID 53938

Reaktionsgleichung

Reaktionsgleichung von HRID 53938
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:13]2[S:14][CH:15]=[C:16]([C:18](OCC)=[O:19])[N:17]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>C1(C)C=CC=CC=1.C1COCC1>[N:7]1([C:13]2[S:14][CH:15]=[C:16]([CH2:18][OH:19])[N:17]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Komponenten

5

Edukt 2

HCID 15053544Ethyl 2-(morpholin-4-yl)-1,3-thiazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 10608093[2-(Morpholin-4-yl)-1,3-thiazol-4-yl]methanolAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customquenched cautiously with aqueous Rochelle's salts
  2. additiondiluted with chloroform
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-72d56d31923d464eb7b837cc806e8111
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05621109

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