Tetrahydrofuran → 5-Chloro-2-methyl-3-pyridinemethanol

HRID 1362678Notes

Reaction equation

HRID 1362678 reaction equation
C1COCC1.[CH3:6][C:7]1[C:12]([C:13](OC)=[O:14])=[CH:11][C:10]([Cl:17])=[CH:9][N:8]=1.[H-].[Li+].[B+3].[H-].[H-].[H-]>O>[Cl:17][C:10]1[CH:11]=[C:12]([CH2:13][OH:14])[C:7]([CH3:6])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10867045Methyl 5-chloro-2-methylnicotinateHCID 178419132HCID 178419132, compound

Product 1

HCID 669614925-Chloro-2-methyl-3-pyridinemethanolYield 30.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a THF (30 mL) solution of 5-chrolo-2-methyl nicotinic acid methyl ester (CAS# 350597-49-8) (1.0 g), boron lithium hydride (0.153 g) was added at 0° C. The reaction solution was agitated at room temperature for 2 hours. The reaction solution was added to iced water and the reaction solution was extracted with ethyl acetate. The obtained organic layer was washed with a saturated salt solution, and it concentrated under reduced pressure after dried over anhydrous magnesium sulfate. 0.26 g of the title compound was obtained by the residue was purified by silica gel chromatography (elution solvent: heptane-ethyl acetate system).

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with a saturated salt solution, and it
  3. concentrationconcentrated under reduced pressure
  4. dry with materialafter dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-f6b0f3bc896e467c96910459ee355ab9
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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