Water → (2-(Benzyloxy)pyridin-4-yl)methanol

HRID 852067Notes

Reaction equation

HRID 852067 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][N:24]=1)[C:18](OC)=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C(OCC)C>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH2:18][OH:19])[CH:22]=[CH:23][N:24]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22926252Methyl 2-(benzyloxy)isonicotinate

Product 1

HCID 16096699(2-(Benzyloxy)pyridin-4-yl)methanolYield 82.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of lithium aluminum hydride (3.0 g) in diethyl ether (300 mL) was cooled on ice in a nitrogen atmosphere, and then a solution of methyl 2-(benzyloxy)isonicotinate (13.07 g) in diethyl ether (50 mL) wad added dropwise thereinto over 1.5 hours. After stirring for 1 hour, water (3 mL), 5N aqueous sodium hydroxide solution (3 mL) and water (9 mL) were successively added dropwise thereinto under ice-cooling. The insoluble matters were filtered off and washed with diethyl ether, and the filtrate was concentrated. After diethyl ether was added to the residue, the solution was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale red oil (9.57 g).

Workup

  1. temperaturewas cooled on ice in a nitrogen atmosphere
  2. temperatureunder ice-cooling
  3. filtrationThe insoluble matters were filtered off
  4. washwashed with diethyl ether
  5. concentrationthe filtrate was concentrated
  6. additionAfter diethyl ether was added to the residue
  7. dry with materialthe solution was dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-732f130ee2ca4185933be294fbcfc74d
Source dataset
uspto-grants-2007_08
Patent number
US07253178B2

Reaction notes

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