Methyl 4-(trifluoromethyl)nicotinate → (4-(Trifluoromethyl)pyridin-3-yl)methanol

HRID 1292044Notes

Reaction equation

HRID 1292044 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]([F:20])([F:19])[C:9]1[C:14]([C:15](OC)=[O:16])=[CH:13][N:12]=[CH:11][CH:10]=1>C1COCC1>[OH:16][CH2:15][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]=1[C:8]([F:20])([F:7])[F:19]

Participants

4

Reactant 2

HCID 2775680Methyl 4-(trifluoromethyl)nicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 18914105(4-(Trifluoromethyl)pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of LAH (0.64 g, 17.0 mmol) in THF (30 mL) at -78° C. was added dropwise methyl 4-trifluoromethylnicotinate (1.74 g, 8.48 mmol) in THF (20 mL). The mixture was stirred for 1 h then carefully quenched with aqueous NaHCO3 (80 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give 3-hydroxymethyl-4-trifluoromethylpyridine as an oil (TLC: Rf = 0.35 (1:1 hexane:EtOAc)).

Workup

  1. customthen carefully quenched with aqueous NaHCO3 (80 mL)
  2. extractionextracted with CH2Cl2 (3×100 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-825762a821df49e381027f649ef3fc7c
Source dataset
uspto-grants-1998_05
Patent number
US05756497

Reaction notes

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