Aluminium lithium hydride → (6-(4-(Trifluoromethyl)phenyl)pyridin-3-yl)methanol

HRID 1669237Notes

Reaction equation

HRID 1669237 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:6][CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:18][C:16]([F:17])([F:19])[C:13]1[CH:12]=[CH:11][C:10]([C:7]2[N:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21936350Methyl 6-(4-(trifluoromethyl)phenyl)nicotinate

Product 1

HCID 21935952(6-(4-(Trifluoromethyl)phenyl)pyridin-3-yl)methanolYield 103.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-trifluoromethyl-phenyl)-nicotinic acid methyl ester (13.7 g, 48.7 mmol) in THF (100 mL) is added LiAlH4 (1.0 M in THF, 50 mL, 50 mmol) at 0˜5° C., the reaction mixture is stirred for 2 hr, quenched by water and 5N NaOH (0.5 mL) carefully. The resulting mixture is diluted with ethyl acetate and filtered through celite. Concentration of the filtrate gives [6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol (12.8 g).

Workup

  1. customquenched by water and 5N NaOH (0.5 mL) carefully
  2. additionThe resulting mixture is diluted with ethyl acetate
  3. filtrationfiltered through celite

Sources & evidence

ORD record
ord-09f11046e7fe4168b6a421aacb549d8d
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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