Trifluoroacetic acid → HCID 74888431, compound

HRID 1526581Notes

Reaction equation

HRID 1526581 reaction equation
FC(F)(F)C(O)=O.COC1C=CC(C[O:15][C:16]2[CH:17]=[C:18]([CH3:24])[C:19]([CH:22]=[CH2:23])=[N:20][CH:21]=2)=CC=1>C1(OC)C=CC=CC=1>[CH3:24][C:18]1[CH:17]=[C:16]([OH:15])[CH:21]=[N:20][C:19]=1[CH:22]=[CH2:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86732290HCID 86732290, compound

Product 1

HCID 74888431HCID 74888431, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (1.25 mL, 5 times) was added to a stirred solution of 5-((4-methoxybenzyl)oxy)-3-methyl-2-vinylpyridine (250 mg, 0.00098 mmol) in anisole (0.5 mL). The reaction mixture was stirred for 2 h at ambient temperature. After completion of the reaction, the reaction mixture was concentrated and quenched with saturated NaHCO3 solution (2 ml). The reaction mixture was extracted with ethyl acetate (2×10 mL) and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was triturated with pentane to afford 5-methyl-6-vinylpyridin-3-ol as an off white solid (100 mg, 76%). MS m/z=136.15 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated
  3. customquenched with saturated NaHCO3 solution (2 ml)
  4. extractionThe reaction mixture was extracted with ethyl acetate (2×10 mL)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was triturated with pentane

Sources & evidence

ORD record
ord-26b6d2c942f64c77bb693b0842afa2f8
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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