Trimethylsulfonium iodide → 2-(Pyrid-3-yl)-4-methylbutane-1,2-diol

HRID 1613643Notes

Reaction equation

HRID 1613643 reaction equation
[CH:1]([C:4]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5])([CH3:3])C.C[C:13]([O-:16])(C)C.[K+].[I-].[CH3:19][S+](C)C>C(O)(C)(C)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:4]([OH:5])([CH2:1][CH2:3][CH3:19])[CH2:13][OH:16])[CH:7]=1

Participants

5

Reactant 3

HCID 75127Trimethylsulfonium iodideHCID 122813372-Methyl-1-(pyridin-3-yl)propan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 197742092-(Pyrid-3-yl)-4-methylbutane-1,2-diol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
65 °C

Procedure

20 g (0.134 mol) of 3-pyridyl isopropyl ketone and 30.2 g (0.268 mol) of potassium tert-butylate were dissolved in 200 ml of tert-butanol. Thereafter, 37.4 g (0.208 mol) of trimethylsulfonium iodide were added and the mixture was heated at 65° C. for 1.5 hours. The inorganic salts were separated off and the reaction solution was evaporated down, after which 75 ml of half-concentrated H2SO4 were added to the crude product and the mixture was heated at 60°-70° C. for 8 hours. The pH was then brought to 9 with 4N NaOH solution and extraction was carried out with methylene chloride. The organic phase was dried and evaporated down and the product was then purified by chromatography.

Workup

  1. customThe inorganic salts were separated off
  2. customthe reaction solution was evaporated down
  3. additionafter which 75 ml of half-concentrated H2SO4 were added to the crude product
  4. temperaturethe mixture was heated at 60°-70° C. for 8 hours
  5. extractionThe pH was then brought to 9 with 4N NaOH solution and extraction
  6. customThe organic phase was dried
  7. customevaporated down
  8. customthe product was then purified by chromatography

Sources & evidence

ORD record
ord-43d2d0124b4745cc8e0a604e4099bc34
Source dataset
uspto-grants-1993_03
Patent number
US05194441

Reaction notes

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