Ethyl 2-methylnicotinate → (2-Methylpyridin-3-yl)methanol

HRID 1292041Notes

Reaction equation

HRID 1292041 reaction equation
[CH3:1][C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](OCC)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:5][CH2:4][C:3]1[C:2]([CH3:1])=[N:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 74401Ethyl 2-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 302564(2-Methylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of ethyl 2-methylnicotinate (1.50 g, 9.09 mmol) in THF (65 mL) at 0° C. was added LAH (9.1 mL of a 1.0 M solution in THF; 9.1 mmol). The mixture was stirred at ambient temperature for 18 h and then quenched by the sequential addition of ethyl acetate (0.1 mL), water (0.1 mL), 15% aqueous NaOH (0.1 mL) and water (0.28 mL). The solids were removed by filtration through celite and the filtrate solvents were removed under reduced pressure. 3-Hydroxymethyl-2-methylpyridine was obtained as an oil (TLC: Rf = 0.40 (5:95 MeOH:CH2Cl2)).

Workup

  1. customquenched by the sequential addition of ethyl acetate (0.1 mL), water (0.1 mL), 15% aqueous NaOH (0.1 mL) and water (0.28 mL)
  2. customThe solids were removed by filtration through celite
  3. customthe filtrate solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-68dedc06a44d4149bf1a5c89fd43e4d9
Source dataset
uspto-grants-1998_05
Patent number
US05756497

Reaction notes

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