Aluminium lithium hydride → HCID 57443403, compound

HRID 2070979Notes

Reaction equation

HRID 2070979 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14](OC)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:13]([CH2:14][OH:15])[CH:12]=[N:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57421820HCID 57421820, compound

Product 1

HCID 57443403HCID 57443403, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 363 mg (1.49 mmol) of methyl 5-(benzyloxy)nicotinate in 10 mL of THF at 0° C. was added 141 mg (3.71 mmol) of LiAlH4. The ice bath was removed, and after 55 min., 20.5 mg of LiAlH4 was added. After 40 min., the reaction was quenched by adding successively 160 μL of H2O, 160 μL of 15% aqueous NaOH, and 480 μL of brine. Purification by flash silica gel chromatography (2 mL MeOH/100 mL CHCl3) provided 250 mg of (5-(benzyloxy)pyridin-3-yl)methanol (yellow oil) in 78% yield.

Workup

  1. customThe ice bath was removed
  2. addition20.5 mg of LiAlH4 was added
  3. waitAfter 40 min.
  4. customthe reaction was quenched
  5. additionby adding successively 160 μL of H2O, 160 μL of 15% aqueous NaOH, and 480 μL of brine
  6. customPurification by flash silica gel chromatography (2 mL MeOH/100 mL CHCl3)

Sources & evidence

ORD record
ord-816aee39f54a44189fe1b92f8784bc4f
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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