2,2-Dimethoxypropane → Ethyl 2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxane-5-carboxylate

HRID 64442Notes

Reaction equation

HRID 64442 reaction equation
[OH:1][CH2:2][C:3]([CH2:15][OH:16])([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].CO[C:19](OC)([CH3:21])[CH3:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:20][C:19]1([CH3:21])[O:1][CH2:2][C:3]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:15][O:16]1

Participants

5

Reactant 3

HCID 64952,2-Dimethoxypropane2×HCID 521998p-Toluenesulfonic acid monohydrate2×HCID 86713459Ethyl 3-hydroxy-2-(hydroxymethyl)-2-(pyridin-3-yl)propanoate

Product 1

HCID 71108573Ethyl 2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxane-5-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 1.25 g of ethyl 3-hydroxy-2-(hydroxymethyl)-2-(pyridin-3-yl)propanoate in 13 ml of acetone were added 0.75 ml of 2,2-dimethoxypropane and 105 mg of p-toluenesulfonic acid monohydrate, followed by stirring for 12 hours. Then, 1.06 g of p-toluenesulfonic acid monohydrate was added thereto, followed by stirring for 6 hours. Further, 0.75 ml of 2,2-dimethoxypropane was added thereto, followed by stirring at 50° C. for 30 minutes, and the solvent was evaporated under reduced pressure. To the obtained residue were added 13 ml of acetone and 0.78 ml of 2-methoxy-1-propene at room temperature, followed by stirring for 30 minutes. To the reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.16 g of ethyl 2,2-dimethyl-5-(pyridin-3-yl)-1,3-dioxane-5-carboxylate.

Workup

  1. stirringby stirring for 6 hours
  2. stirringby stirring at 50° C. for 30 minutes
  3. customthe solvent was evaporated under reduced pressure
  4. additionTo the obtained residue were added 13 ml of acetone and 0.78 ml of 2-methoxy-1-propene at room temperature
  5. stirringby stirring for 30 minutes
  6. additionTo the reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  7. customa layer separation operation
  8. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine in this order
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a8e23039bd92483987f31909a739975a
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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