Ethyl Acetate → 5-(Methoxymethyl)-3-(3-pyridinyl)-2-oxazolidinone

HRID 1900080Notes

Reaction equation

HRID 1900080 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7]C(=O)OCC)[CH:2]=1.[CH3:13][O:14][CH2:15][CH:16]1[CH2:20][O:19][C:18](=O)[O:17]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>O>[CH3:13][O:14][CH2:15][CH:16]1[O:17][C:18](=[O:19])[N:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:20]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 235275ethyl pyridin-3-ylcarbamateHCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-one

Product 1

HCID 233718445-(Methoxymethyl)-3-(3-pyridinyl)-2-oxazolidinoneYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.8 g of ethyl pyridin-3-yl-carbamate, 20 g of 4-methoxymethyl-1,3-dioxolan-2-one and 2.8 g of potassium carbonate was heated to 160° for 3 h. The mixture was cooled and treated with ethyl acetate and water. The phases were separated, the aqueous phase was extracted with ethyl acetate and the organic phase was washed with saturated sodium chloride solution. The organic phases were combined, dried with magnesium sulfate and concentrated. Chromatography of the residue (21 g) on silica gel with ethyl acetate/methanol mixtures (1:0-20:1) yielded 17.6 g of (RS)-5-methoxymethyl-3-pyridin-3-yl-oxazolidin-2-one which was recrystallized from diethyl ether. M.p.: 65°-66°.

Workup

  1. temperaturewas heated to 160° for 3 h
  2. temperatureThe mixture was cooled
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. washthe organic phase was washed with saturated sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d73a93bad73545f995fbe6d612e2a198
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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