Sodium sulfate decahydrate → (2-Ethyl-5-methyl-1,3-thiazol-4-YL)methanol

HRID 2221702Notes

Reaction equation

HRID 2221702 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([CH3:12])=[C:6]([C:8](OC)=[O:9])[N:7]=1)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([C:3]1[S:4][C:5]([CH3:12])=[C:6]([CH2:8][OH:9])[N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23076482Methyl 2-ethyl-5-methyl-1,3-thiazole-4-carboxylate

Product 1

HCID 23076454(2-Ethyl-5-methyl-1,3-thiazol-4-YL)methanolYield 53.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-ethyl-5-methyl-1,3-thiazole-4-carboxylate (8.1 g) in tetrahydrofuran (400 mL) was added lithium aluminum hydride (1.8 g) at 0° C., and the mixture was stirred for 2 hrs. Sodium sulfate decahydrate (15.5 g) was added to the reaction mixture, and the mixture was stirred for 1 hr. The reaction mixture was filtered and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (5:95-70:30, v/v) to give (2-ethyl-5-methyl-1,3-thiazol-4-yl)methanol as a yellow oil (3.7 g, yield 53%).

Workup

  1. stirringthe mixture was stirred for 1 hr
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. washeluted with ethyl acetate-hexane (5:95-70:30, v/v)

Sources & evidence

ORD record
ord-0a9aa26d011b47ac84539a6e84c17b2e
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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