Water → (6-Methylpyridin-3-yl)methanol

HRID 2101407Notes

Reaction equation

HRID 2101407 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][N:9]=1.CCOC(C)=O.O>C1COCC1.C(OCC)C>[CH3:7][C:8]1[N:9]=[CH:10][C:11]([CH2:12][OH:13])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 231548Methyl 6-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanolYield 62.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of lithium aluminum hydride (1 M in diethyl ether, 80 mL, 80 mmol) in 20 mL THF at −78° C. under argon, a solution of methyl 6-methylnicotinate (6.05 g, 40 mmol) in 60 mL diethyl ether was added over 1 h. The resulting reaction mixture was stirred at −78° C. for 1 h before 12 mL EtOAc was added over 10 min. The reaction mixture was allowed to warm up to 0° C. and 12 mL water was added drop-wise over 10 min. The resulting mixture was stirred for 30 min, then filtered through Celite. The filtrate was dried (Na2SO4), filtered and concentrated to obtain 3.07 g (62%) of the title compound as an off-white solid. HPLC: retention time=0.19 min.

Workup

  1. customThe resulting reaction mixture
  2. additionwas added over 10 min
  3. filtrationfiltered through Celite
  4. dry with materialThe filtrate was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-875931f2664d4ef9bdb7700578f77af3
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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