Lithium aluminum hydride → (2-Chloropyridin-3-yl)methanol

HRID 227749Notes

Reaction equation

HRID 227749 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[AlH4-].[Li+]>C1COCC1>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 762582-Chloronicotinic acid

Product 1

HCID 2763647(2-Chloropyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-chloronicotinic acid (8.00 g, 51.0 mmol) in THF (120 mL) at 0° C. under nitrogen was slowly added lithium tetrahydroaluminate (51 mL, 51 mmol) over five minutes. The reaction was allowed to warm to RT over 2 h and was monitored by TLC. The reaction was quenched by addition of small amounts of ice followed by water. Extracted product into EtOAc, washed 2×H2O , 1×NaCl, dried with Mg2SO4, filtered through fritted funnel, and concentrated the solution to yield (2-chloropyridin-3-yl)methanol as an orange oil. Used without further purification.

Workup

  1. customat 0° C.
  2. customover five minutes
  3. customThe reaction was quenched by addition of small amounts of ice
  4. washExtracted product into EtOAc, washed 2×H2O , 1×NaCl
  5. dry with materialdried with Mg2SO4
  6. filtrationfiltered through fritted funnel
  7. concentrationconcentrated the solution

Sources & evidence

ORD record
ord-5c418c1280b1450e9bd33b35ed0e4e5d
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

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