HCID 18922481, compound → HCID 18922526, compound

HRID 1290003Notes

Reaction equation

HRID 1290003 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[S:6][C:7]=1[C:8](OCC)=[O:9].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:9][CH2:8][C:7]1[S:6][C:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 18922481HCID 18922481, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 18922526HCID 18922526, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-methoxy-2-(4-pyridyl)-thiazole-5-carboxylate (169 mg, 0.639 mmol) in THF (4 mL) cooled in an ice-bath was added lithium aluminum hydride portionwise (48 mg, 1.26 mmol). After stirring for 15 minutes at ice temperature, excess LAH was destroyed by sequential addition of water (48 μL), 15% aqueous NaOH (48 μL), and water (144 μL). The mixture was diluted with THF, filtered through a pad of Celite, and evaporated. The title compound was purified by flash chromatography eluting with 25% acetone/hexane.

Workup

  1. customwas destroyed by sequential addition of water (48 μL), 15% aqueous NaOH (48 μL), and water (144 μL)
  2. additionThe mixture was diluted with THF
  3. filtrationfiltered through a pad of Celite
  4. customevaporated
  5. customThe title compound was purified by flash chromatography
  6. washeluting with 25% acetone/hexane

Sources & evidence

ORD record
ord-50e8be4282654fb6977983172047f688
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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