Aluminium lithium hydride → HCID 58097157, compound

HRID 1897962Notes

Reaction equation

HRID 1897962 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[N:12]=[C:11]([C:16](OC)=[O:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[N:12]=[C:11]([CH2:16][OH:17])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 46941455HCID 46941455, compound

Product 1

HCID 58097157HCID 58097157, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 500 mg of methyl 4-(benzyloxy)-6-chloropyridine-2-carboxylate (WO2006/046734, page 123, Example 116(5)) in 3 ml of tetrahydrofuran was added 78 mg of lithium aluminum hydride at room temperature, followed by stirring the reaction mixture at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous ammonium chloride solution, water and brine. The ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to give the title compound as a pale yellow solid.

Workup

  1. washwashed with saturated aqueous ammonium chloride solution, water and brine
  2. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-32ab30ac3a22400fb4059947d74677d8
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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