Ethyl Acetate → HCID 18673021, compound

HRID 1058359Notes

Reaction equation

HRID 1058359 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[S:16][C:15]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[N:14][CH:13]=1)=O)C.C(OCC)(=O)C>C(OCC)C>[S:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[C:15]1[S:16][C:12]([CH2:10][OH:9])=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22009660Ethyl 2-(2-thienyl)-5-thiazolecarboxylate

Product 1

HCID 18673021HCID 18673021, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of lithium aluminum hydride (52 mg, 1.25 mmol) in diethyl ether (2 mL) under argon was added 2-(2-thienyl)thiazole-5-carboxylic acid ethyl ester (lit: Robba, M., LeGuen, Y., Bull. Soc. Chim. Fr., 1969(5)1762; 0.3 g, 1.25 mmol) at 0° C. The reaction mixture was allowed to equilibrate to room temperature and was stirred for 24 h. The reaction was re-cooled to 0° C. and was quenched by the careful addition of saturated aqueous ammonium chloride solution dropwise until no further reaction was apparent. The resulting solids were recovered by filtration, washed with diethyl ether and retained for further processing (vide infra). The filtrate was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The solids that were recovered from the ammonium chloride quench were then slurried in ethyl acetate, filtered and washed with ethyl acetate. The resulting filtrate was washed with brine, dried (MgSO4), filtered and evaporated reduced pressure. The solid residues obtained from the work up of both the diethyl ether filtrate and the ethyl acetate filtrate were combined to yield 179 mg (72% yield) of 2-(2-thienyl)thiazole-5-methanol as a yellow solid.

Workup

  1. customto equilibrate to room temperature
  2. customwas quenched by the careful addition of saturated aqueous ammonium chloride solution dropwise until no further reaction
  3. filtrationThe resulting solids were recovered by filtration
  4. washwashed with diethyl ether
  5. washThe filtrate was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe solids that were recovered from the ammonium chloride
  10. customquench
  11. filtrationfiltered
  12. washwashed with ethyl acetate
  13. washThe resulting filtrate was washed with brine
  14. dry with materialdried (MgSO4)
  15. filtrationfiltered
  16. customevaporated reduced pressure
  17. customThe solid residues obtained from the work up of both the diethyl ether filtrate

Sources & evidence

ORD record
ord-259d15fd24e244ff85639280333a8d2f
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

Loading…