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

HRID 2210963Notes

Reaction equation

HRID 2210963 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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, dried 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).

Workup

  1. customquenched cautiously with aqueous Rochelle's salts
  2. additiondiluted with chloroform
  3. filtrationfiltered
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4135e773bb774a78aaa5fe8ae2e8f653
Source dataset
uspto-grants-1995_10
Patent number
US05461067

Reaction notes

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