Aluminium lithium hydride → HCID 21256450, compound

HRID 635846Notes

Reaction equation

HRID 635846 reaction equation
C([O:3][C:4]([C:6]1[N:13]2[C:9]([S:10][CH:11]=[C:12]2[CH3:14])=[N:8][CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:14][C:12]1[N:13]2[C:6]([CH2:4][OH:3])=[CH:7][N:8]=[C:9]2[S:10][CH:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54564036Ethyl 3-methylimidazo[2,1-b][1,3]thiazole-5-carboxylate

Product 1

HCID 21256450HCID 21256450, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-Methylimidazo[2,1-b]thiazole-5-carboxylic acid ethyl ester (Formula C-4) (1.93 g, 9.2 mmol) in dry THF (20 ml) at 0° was treated with LiAlH4 (12.3 mmols, 0.47 gms) and reacted at 25° for 2 hours. The reaction was quenched by serial additions of 2% aqueous.. THF (24 mL), 15% NAOH (0.47 mL), and 2% aqueous THF (1.5 mL). The suspension was filtered and the filtrate was concentrated to a white solid (1.48 gm). The solid was recrystallized from isopropanol to yield pure 3-Methylimidazo[2,1-b]thiazole-5-Methanol (FIG. C-5) (1.18 g), m.p. 161-162°.

Workup

  1. customreacted at 25° for 2 hours
  2. customThe reaction was quenched by serial additions of 2% aqueous
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated to a white solid (1.48 gm)
  5. customThe solid was recrystallized from isopropanol

Sources & evidence

ORD record
ord-f7ceb1ef7602471c979056973fc4303e
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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