Water → 5-Hydroxymethyl-2-(2-methylpropyl)thiazole

HRID 348849Notes

Reaction equation

HRID 348849 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][C:4]1[S:5][C:6]([C:9](OCC)=[O:10])=[CH:7][N:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[OH:10][CH2:9][C:6]1[S:5][C:4]([CH2:3][CH:2]([CH3:14])[CH3:1])=[N:8][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21086091Ethyl 2-isobutylthiazole-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 210859775-Hydroxymethyl-2-(2-methylpropyl)thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 2-(2-methylpropyl)thiazole-5-carboxylate (2.05 g, 9.6 mmol) in THF (10 mL) is added dropwise with stirring to a suspension of lithium aluminum hydride (730 mg, 19 mmol) in dry THF (50 mL) at 0 degrees C. Upon complete addition, the reaction mixture is allowed to stir at 20–25 degrees C. The reaction mixture is cooled to 0 degrees C., and water (0.75 mL), aqueous sodium hydroxide (15%, 0.75 mL), and water (2.25 mL) is added in succession. This mixture is stirred at 0 degrees C. for 1 hour, then filtered through diatomaceous earth, (THF and chloroform). The filtrate is concentrated to give 5-hydroxymethyl-2-(2-methylpropyl)thiazole, MS(ESI): MH+: 172.1.

Workup

  1. additionUpon complete addition
  2. stirringThis mixture is stirred at 0 degrees C
  3. filtrationfiltered through diatomaceous earth, (THF and chloroform)
  4. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-2605659ecac44cc691c1d03ecaa3ad02
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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