Aluminium lithium hydride → HCID 69589367, compound

HRID 860691Notes

Reaction equation

HRID 860691 reaction equation
C([O:3][C:4](=O)[CH:5]([C:7]1[N:8]=[C:9]([C:13]2[CH:14]=[N:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])=[CH:17][CH:18]=2)[S:10][C:11]=1[CH3:12])[CH3:6])C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:16]1[N:15]=[CH:14][C:13]([C:9]2[S:10][C:11]([CH3:12])=[C:7]([CH:5]([CH3:6])[CH2:4][OH:3])[N:8]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69589287HCID 69589287, compound

Product 1

HCID 69589367HCID 69589367, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{2-[6-(2-Fluoro-phenyl)-pyridin-3-yl]-5-methyl-thiazol-4-yl}-propionic acid ethyl ester (2.6 g, 7.03 mmol) in THF (15 mL) is added LiAlH4 (1.0 M in THF, 7.1 mL, 7.1 mmol) at 0–5° C., and then stirred for 2 h. The reaction is then quenched by water and 5 N NaOH, diluted with THF and filtered through a pad of celite. The filtrate is concentrated and purified by column yielding 1.8 g of the product.

Workup

  1. customThe reaction is then quenched by water and 5 N NaOH
  2. additiondiluted with THF
  3. filtrationfiltered through a pad of celite
  4. concentrationThe filtrate is concentrated
  5. custompurified by column

Sources & evidence

ORD record
ord-405e95f1dda74569a2218e0b797829b1
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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