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

HRID 52703

반응식

HRID 52703 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 10608093[2-(Morpholin-4-yl)-1,3-thiazol-4-yl]methanol수율 61.1%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

A solution of 7.0 ml (7.0 immol) 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) δ2.44 (br, 1H), 3.46 (t, J=5 Hz, 4H), 3.81 (t, J=5 Hz, 1H), 4.55 (br s, 2H), 6.45 (s, 1H). Mass spectrum: (M+H)+ =200.

후처리

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

출처 및 근거

ORD 기록
ord-591c9c587f8c44d6979f277b007727be
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616720

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