HCID 10176480, compound → FURO[2,3-B]PYRIDINE-5-METHANOL

HRID 220267Notes

Reaction equation

HRID 220267 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][O:12][C:9]2=[N:10][CH:11]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:12]1[C:9]2=[N:10][CH:11]=[C:6]([CH2:4][OH:3])[CH:7]=[C:8]2[CH:14]=[CH:13]1

Participants

4

Reactant 2

HCID 10176480HCID 10176480, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10057661FURO[2,3-B]PYRIDINE-5-METHANOLYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 1.9 g of furo[2,3-b]pyridine-5-carboxylic acid ethyl ester (GB 2289276) in 30 ml of THF was added dropwise 17.3 ml of a LiAlH4 (2.3M THF) solution at −20° C. The reaction mixture was stirred for 3 h at −20° C. and then quenched by addition of 1M NaOH solution. The resulting mixture was filtrated over a pad of celite, washed with THF and the filtrate was concentrated in vacuo. Purification by CC using EtOAc yielded 0.5 g of furo[2,3-b]pyridin-5-yl-methanol as yellow oil.

Workup

  1. customquenched by addition of 1M NaOH solution
  2. filtrationThe resulting mixture was filtrated over a pad of celite
  3. washwashed with THF
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification by CC

Sources & evidence

ORD record
ord-36f0f37fe9dd4c2e82a3f88f2c73150e
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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