Water → 3-(2-Methyl-1,3-thiazol-5-yl)propan-1-ol

HRID 437943Notes

Reaction equation

HRID 437943 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][C:15](OC)=[O:16])=[CH:11][N:12]=1.O>O1CCCC1>[CH3:7][C:8]1[S:9][C:10]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 20388954HCID 20388954, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 203889553-(2-Methyl-1,3-thiazol-5-yl)propan-1-olYield 69.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
10 °C

Procedure

A mixture of 125 ml of tetrahydrofuran and 3.42 g of lithium aluminum hydride was cooled to about 10° C. and a mixture of 10.9 g of methyl 2-methyl-5-thiazolepropanoate in 70 ml of tetrahydrofuran was slowly added thereto with stirring while keeping the temperature between 10-15° C. The mixture was then stirred for about 30 minutes and tetrahydrofuran containing 20% of water was slowly added. The mixture was filtered and the filter was washed with ethyl acetate. The filtrate was dried over magnesium sulfate and concentrated to dryness under reduced pressure to obtain 8.4 g of a raw product which was rectified under reduced pressure to obtain 6.4 g of 2-methyl-5-thiazole-propanol with a boiling point of 106° C. at 0.05 mm Hg.

Workup

  1. additionwas slowly added
  2. custombetween 10-15° C
  3. stirringThe mixture was then stirred for about 30 minutes
  4. filtrationThe mixture was filtered
  5. washthe filter was washed with ethyl acetate
  6. dry with materialThe filtrate was dried over magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customto obtain 8.4 g of a raw product which

Sources & evidence

ORD record
ord-09a14bcb3ff3490ea13b186cfab958d4
Source dataset
uspto-grants-1977_06
Patent number
US04032643

Reaction notes

Loading…