2,3-Dihydroxybutanedioic Acid → (6-Chloropyridin-3-yl)methanol

HRID 2246778Notes

Reaction equation

HRID 2246778 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6](OCC)=[O:7])=[CH:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(=O)C(C(C(O)=O)O)O>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8752,3-Dihydroxybutanedioic AcidHCID 2799611Ethyl 6-chloronicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 177161(6-Chloropyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a −78° C. solution of ethyl 6-chloronicotinate (10 g) in 250 mL of THF was slowly added 126 mL of lithium aluminium hydride (1.5 M in toluene). The mixture was stirred at 0° C. for 1 hour. Poured into saturated aqueous tartaric acid (200 mL) and extracted with ethyl acetate (2×200 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by chromatography on SiO2 using ethyl acetate and hexanes (1:2 to 1:1) to yield the title compound.

Workup

  1. customTo a −78° C.
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by chromatography on SiO2

Sources & evidence

ORD record
ord-19889396ab604463b9bf52060ca5a0e3
Source dataset
uspto-grants-2010_03
Patent number
US07687524B2

Reaction notes

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