Sodium Hydroxide → 5-(Hydroxymethyl)-4-thiazoleethanol

HRID 546436Notes

Reaction equation

HRID 546436 reaction equation
Br[C:2]1[S:3][C:4]([C:12](OC)=[O:13])=[C:5]([CH2:7][C:8](OC)=[O:9])[N:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[OH:9][CH2:8][CH2:7][C:5]1[N:6]=[CH:2][S:3][C:4]=1[CH2:12][OH:13]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 22934839Methyl 2-bromo-4-(2-methoxy-2-oxoethyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 178423785-(Hydroxymethyl)-4-thiazoleethanolYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 2-bromo-5-methoxycarbonyl-thiazole-4-acetate (23.4 g) in tetrahydrofuran (500 ml) was added dropwise over 1 hour to a suspension of lithium aluminum hydride (9.03 g) in tetrahydrofuran (500 ml) under ice cooling. After stirring for additional 1 hour under ice cooling, water (9 ml), a 35% aqueous solution (9 ml) of sodium hydroxide and water (27 ml) were successively added, and the mixture was stirred at room temperature for 1 hour. After anhydrous magnesium sulfate was added to the reaction mixture, and the resultant mixture was stirred, insoluble matter was removed by filtration with Celite, and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (methanol:dichloromethane=7:93) to obtain the title compound (8.64 g) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. custominsoluble matter was removed by filtration with Celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by column chromatography on silica gel (methanol:dichloromethane=7:93)

Sources & evidence

ORD record
ord-a9c7627569624d1596b808ccfe55ad0f
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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