Aluminium lithium hydride → HCID 69139516, compound

HRID 854576Notes

Reaction equation

HRID 854576 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:7]=[C:8]([C:12]2[CH:13]=[N:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])=[CH:16][CH:17]=2)[S:9][C:10]=1[CH3:11])C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:15]1[N:14]=[CH:13][C:12]([C:8]2[S:9][C:10]([CH3:11])=[C:6]([CH2:5][CH2:4][OH:3])[N:7]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69141350HCID 69141350, compound

Product 1

HCID 69139516HCID 69139516, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {2-[6-(2-Fluoro-phenyl)-pyridin-3-yl]-5-methyl-thiazol-4-yl}-acetic acid ethyl ester (1.7 g, 4.77 mmol) in THF (10 mL) is added LiAlH4 (1.0 M in THF, 4.8 mL, 4.8 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 1.4 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-b091665e05e843fbb78a6390288dd98d
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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