Methyl 6-methylnicotinate → (6-Methylpyridin-3-yl)methanol

HRID 1845128Notes

Reaction equation

HRID 1845128 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][N:3]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C(OCC)C>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 231548Methyl 6-methylnicotinateHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl 6-methylnicotinate (25 g, 0.16 mol) in ethyl ether (620 mL) under nitrogen was added dropwise sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al®) (65 wt. % in toluene, 110 mL, 0.37 mol) at room temperature. The mixture was then heated to reflux for 1.5 hr. After cooling, the reaction mixture was quenched with water (500 mL) at 0° C. and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel column to afford the title compound.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 1.5 hr
  3. temperatureAfter cooling
  4. customthe reaction mixture was quenched with water (500 mL) at 0° C.
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-47c2feb23de7459ab58fd363dc0275a8
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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