Ethylene Glycol → Methyl 4-[3-(2-methyldioxolan-2-yl)-phenoxy]-6-methoxy-pyrimidin-5-yl-acetate

HRID 1078196Notes

Reaction equation

HRID 1078196 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[O:7][C:8]1[C:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:12]([O:19][CH3:20])[N:11]=[CH:10][N:9]=1)(=[O:3])[CH3:2].[CH2:24](O)[CH2:25][OH:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:2][C:1]1([C:4]2[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=2)[O:7][C:8]2[C:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:12]([O:19][CH3:20])[N:11]=[CH:10][N:9]=2)[O:26][CH2:25][CH2:24][O:3]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 53697352Methyl 4-(3-acetylphenoxy)-6-methoxy-pyrimidin-5-yl-acetate

Product 1

HCID 22358415Methyl 4-[3-(2-methyldioxolan-2-yl)-phenoxy]-6-methoxy-pyrimidin-5-yl-acetateYield 95.6%

Procedure

A mixture of methyl 4-(3-acetylphenoxy)-6-methoxy-pyrimidin-5-yl-acetate (15.0 g, 47 mmol), ethylene glycol (7.9 ml, 140 mmol) and p-toluene sulfonic acid is refluxed, removing the water azeotropically. After two hours the organic phase is washed with saturated sodium carbonate solution, dried (MgSO4) and evaporated to give the methyl 4-[3-(2-methyldioxolan-2-yl)-phenoxy]-6-methoxy-pyrimidin-5-yl-acetate as a yellow oil (16.2 g).

Workup

  1. temperatureis refluxed
  2. customremoving the water azeotropically
  3. washAfter two hours the organic phase is washed with saturated sodium carbonate solution
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-4a97d9a904f342479ab0df5864139367
Source dataset
uspto-grants-1996_08
Patent number
US05547919

Reaction notes

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