Sodium Bicarbonate → 2-(3-methoxy-phenoxymethyl)-1H-imidazole

HRID 2101513Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH2:7][C:8]1[N:9](C2CCCO2)[CH:10]=[CH:11][N:12]=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH2:7][C:8]1[NH:12][CH:11]=[CH:10][N:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-(3-methoxy-phenoxymethyl)-1-(tetrahydro-furan-2-yl)-1H-imidazole 1N HCl (20 mL) and THF (20 mL) was stirred at 50° C. for 24 h. Saturated NaHCO3 was added to adjust the pH to 8. The mixture was extracted with CH2Cl2 (3×100 mL). The combined CH2Cl2 extracts were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 1:2 hexane/EtOAc) to provide the desired 2-(3-methoxy-phenoxymethyl)-1H-imidazole (2.40 g, 92%) as a white solid: ESI MS m/z 205 [C11H12N2O2+H]+.

Workup

extractionThe mixture was extracted with CH2Cl2 (3×100 mL)
dry with materialThe combined CH2Cl2 extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (silica gel, 1:2 hexane/EtOAc)

Sources & evidence

ORD record: ord-2df5f1508bf34902a071bdc8a9ceaa10
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572921B2

Reaction notes

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