Aluminium lithium hydride → (2-Ethyl-1,3-thiazol-5-yl)methanol

HRID 2072388Notes

Reaction equation

HRID 2072388 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[S:10][C:11]([C:14](OC)=[O:15])=[CH:12][N:13]=1)[CH3:8]>O1CCCC1>[CH2:7]([C:9]1[S:10][C:11]([CH2:14][OH:15])=[CH:12][N:13]=1)[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 21408257HCID 21408257, compound

Product 1

HCID 21408258(2-Ethyl-1,3-thiazol-5-yl)methanolYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.4 g of mixed lithium aluminum hydride was added under nitrogen to a solution of 11.3 g of methyl 2-ethyl-thiazole-5-carboxylate in 100 ml of anhydrous tetrahydrofuran at 20 to 25° C and the mixture was refluxed for 1 1/2 hours. After cooling the mixture, excess lithium aluminum hydride was destroyed by the addition of ethyl acetate. The mixture was added to water and was vacuum filtered. The recovered precipitate was empasted with ethyl acetate and then with a methanol-methylene chlorine mixture. The filtrate was washed with water, dried and evaporated to dryness to obtan 9.5 g of an oil which was rectified under reduced pressure to obtain 8.9 g of 2-ethyl-thiazole-5-methanol with a boiling point of 78° C at 0.1 mm Hg.

Workup

  1. temperaturethe mixture was refluxed for 1 1/2 hours
  2. customwas destroyed by the addition of ethyl acetate
  3. additionThe mixture was added to water
  4. filtrationfiltered
  5. washThe filtrate was washed with water
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-49c31ad84948443cb38705d0e2a7dc76
Source dataset
uspto-grants-1977_09
Patent number
US04051249

Reaction notes

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