Water → (2-Propyl-1,3-thiazol-5-yl)methanol

HRID 1076668Notes

Reaction equation

HRID 1076668 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:10]1[S:11][C:12]([C:15](OCC)=[O:16])=[CH:13][N:14]=1)[CH2:8][CH3:9].C(OCC)(=O)C.O>CCOCC>[CH2:7]([C:10]1[S:11][C:12]([CH2:15][OH:16])=[CH:13][N:14]=1)[CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 21413783Ethyl 2-propylthiazole-5-carboxylate

Product 1

HCID 22134228(2-Propyl-1,3-thiazol-5-yl)methanolYield 52%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5.8 g of mixed lithium aluminum hydride were added with stirring under a nitrogen atmosphere to 150 ml of anhydrous ether and a solution of 15.1 g of ethyl 2-propyl-thiazole-5-carboxylate in 30 ml of anhydrous ether was added thereto dropwise. The mixture was stirred for 2 hours, cooled and then 20 ml of ethyl acetate followed by 20 ml of water were added. The organic phase was decanted after filtering off the precipitate formed and the ether phase was dried over magnesium sulfate and evaporated to dryness under reduced pressure. The residue was distilled to obtain 6.2 g of 2-propyl-thiazole-5-methanol with a boiling point of 86°C at 0.01 mmHg. The product could be used to fill capsules with 500 mg of the said product and sufficient polyoxyethyleneglycol to fill the capsules.

Workup

  1. temperaturecooled
  2. additionwere added
  3. customThe organic phase was decanted
  4. filtrationafter filtering off the precipitate
  5. customformed
  6. dry with materialthe ether phase was dried over magnesium sulfate
  7. customevaporated to dryness under reduced pressure
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-b64439b927e54d25b61a453eb2f69bfc
Source dataset
uspto-grants-1976_05
Patent number
US03957809

Reaction notes

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