Methyl 6-chloropyridine-3-carboxylate → (6-Chloropyridin-3-yl)methanol

HRID 1504600Notes

Reaction equation

HRID 1504600 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][N:9]=1>C1COCC1>[Cl:7][C:8]1[N:9]=[CH:10][C:11]([CH2:12][OH:13])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 177161(6-Chloropyridin-3-yl)methanolYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of LiAlH4 (1.5 g, 40 mmol) in THF (80 mL) was added methyl 6-chloronicotinate (1.56 g, 10 mmol) slowly at 0-5□ under N2 atmosphere. The reaction mixture was stirred at rt for 3 h before it was quenched with 15% NaOH and water. The mixture was filtered through Celite® and the cake was washed with EtOAc (100 mL×3). The filtrate was washed with brine (200 mL), dried and concentrated to give the desired product as yellow oil (1 g, 70%). [LCMS: RtA=0.88 min, m/z 144.2 [M+H]+].

Workup

  1. customwas quenched with 15% NaOH and water
  2. filtrationThe mixture was filtered through Celite®
  3. washthe cake was washed with EtOAc (100 mL×3)
  4. washThe filtrate was washed with brine (200 mL)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2aecb7504a9b4beb90e5a5ed574a021f
Source dataset
uspto-grants-2015_12
Patent number
US09216182B2

Reaction notes

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