Aluminium lithium hydride → (4-Phenyl-1,3-thiazol-2-yl)methanol

HRID 868927Notes

Reaction equation

HRID 868927 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:12](OCC)=[O:13])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][OH:13])[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 24730326Ethyl 4-phenyl-1,3-thiazole-2-carboxylate

Product 1

HCID 698895(4-Phenyl-1,3-thiazol-2-yl)methanolYield 109.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 4-phenylthiazole-2-carboxylate (1 g, 4.3 mmol) in anhydrous THF was added LiAlH4 and the mixture was stirred for 1 hour. The reaction was quenched with water, extracted with EtOAc and dried over anhydrous sodium sulfate. The solution was concentrated under vacuum to afford (4-phenylthiazol-2-yl)methanol as a white solid (0.9 g). MS (ESI) m/z 191 (M+H+).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-2e11ec2db35248658c21fc491d8be895
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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