Triethylamine → (5-(Trifluoromethyl)pyridin-3-yl)methanol

HRID 2207023Notes

Reaction equation

HRID 2207023 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH:11]=1)[C:8](O)=[O:9].C(N(CC)CC)C.ClC(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1C=CC=CC=1>[F:12][C:2]([F:1])([F:13])[C:3]1[CH:11]=[C:7]([CH2:8][OH:9])[CH:6]=[N:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 109763055-(Trifluoromethyl)nicotinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 14761463(5-(Trifluoromethyl)pyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5-(trifluoromethyl)nicotinic acid (1.0 g, 5.23 mmol) and triethylamine (0.802 mL, 5.75 mmol) in benzene was added ethyl chloroformate (0.548 mL, 5.75 mmol) and the reaction was stirred 1 hour at room temperature. The reaction was filtered to remove salts and concentrated to dryness. The residue was taken up in tetrahydrofuran and cooled to −78° C. Lithium aluminum hydride (2M in THF, 2.88 mL, 5.75 mmol) was added dropwise and aged 0.5 hour. Reaction was quenched with water and stirred with 0.5N NaOH for 1 hour. The product was extracted with ethyl acetate (2×), washed brine, dried over sodium sulfate and concentrated to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calc'd for C7H6F3NO: 178.04; found: 178.06.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove salts
  3. concentrationconcentrated to dryness
  4. temperaturecooled to −78° C
  5. customReaction
  6. customwas quenched with water
  7. stirringstirred with 0.5N NaOH for 1 hour
  8. extractionThe product was extracted with ethyl acetate (2×)
  9. washwashed brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-46c0d04867554b48823e10e8cfb66d38
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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