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

HRID 1957169Notes

Reaction equation

HRID 1957169 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-0c627677f952478880bee3ba979f587c
Source dataset
uspto-grants-1998_07
Patent number
US05783580

Reaction notes

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