Methanol → (2,6-Dichloropyridin-3-yl)methanol

HRID 1368249Notes

Reaction equation

HRID 1368249 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[N:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].CO>O1CCCC1>[Cl:7][C:8]1[C:9]([CH2:10][OH:11])=[CH:13][CH:14]=[C:15]([Cl:17])[N:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8540472,6-Dichloronicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 12259932(2,6-Dichloropyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1.78 g) was suspended in dry tetrahydrofuran (10 ml), and 2,6-dichloronicotinic acid was added under ice-cooling at an inside temperature of not more than 10° C. The mixture was stirred under ice-cooling for 1 hr and 28% aqueous amonia was added dropwise to the reaction mixture until foams disappeared. Methanol was added and the mixture was stirred at room temperature for 3 hr, and filtered through celite. The mother liquor was concentrated and the residue was applied to flash silica gel column chromatography (silica gel, 200 ml) and eluted with chloroform:ethyl acetate=8:1 to give 2,6-dichloro-3-hydroxymethylpyridine as colorless crystals (2.89 g).

Workup

  1. temperaturecooling at an inside temperature of not more than 10° C
  2. temperaturecooling for 1 hr
  3. addition28% aqueous amonia was added dropwise to the reaction mixture until foams
  4. stirringthe mixture was stirred at room temperature for 3 hr
  5. filtrationfiltered through celite
  6. concentrationThe mother liquor was concentrated
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-8c9d596ef4a048fcaa358db5c25dbf3f
Source dataset
uspto-grants-2003_06
Patent number
US06573274B1

Reaction notes

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