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

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

Reactant 3

HCID 174Ethylene Glycol

HCID 6101p-Toluenesulfonic acid

HCID 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).