Sodium Hydroxide → HCID 58777817, compound

HRID 2368671Notes

Reaction equation

HRID 2368671 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8](O)([CH3:10])[CH3:9].[OH-].[Na+]>I>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131295773-Fluoro-α,α-dimethyl-4-pyridinemethanol

Product 1

HCID 58777817HCID 58777817, compound

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Conditions

Temperature
140 °C

Procedure

2-(3-Fluoro-pyridin-4-yl)-propan-2-ol (from the previous step, 6.40 g, 41.3 mmol) was dissolved in 50 mL of 57% HI aqueous solution. Red phosphorus (4.48 g, 144.0 mmol) was added and the mixture was stirred at 140° C. for 5 hours. The reaction mixture was cooled to room temperature, neutralized with 5N aq NaOH and extracted with ether. The combined organic layers were washed with H2O and brine, then dried over Na2SO4 and concentrated under vacuum. The title compound was obtained by distillation. Spectroscopic data: 1H-NMR (300 MHz, CDCl3): δ ppm 1.27 (d, J=7.04 Hz, 6 H), 3.25 (hept, J=7.04 Hz, 1 H), 7.21 (dd, J=5.44 Hz, 1 H), 8.33-8.36 (m, 2 H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ether
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f5b8552523584530980b7dac2e6044ce
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Reaction notes

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