Ethylene carbonate → 2-{2-[2-(Dimethylamino)ethoxy]phenoxy}ethanol

HRID 1765081Notes

Reaction equation

Cl.[CH2:2]([O:9][C:10]1[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=1[O:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[C:3]1C=CC=CC=1.C1(=O)OCC[O:23]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:17][N:15]([CH3:16])[CH2:14][CH2:13][O:12][C:11]1[CH:18]=[CH:19][CH:20]=[CH:21][C:10]=1[O:9][CH2:2][CH2:3][OH:23]

Participants

Conditions

Temperature: 155 °C

Procedure

To dry DMF (50 mL) was added 2-[2-(dimethylamino)ethoxy]phenol (from Step 1; 5.4 g, 28.0 mmol), ethylene carbonate (3.20 g, 36.4 mmol) and potassium carbonate (3.9 g, 28 mmol) and the mixture was heated at 155° C. for one hour 30 minutes. The solvent from the filtered solution was evaporated under reduced pressure and the resulting residue was dissolved in CHCl3 (50 mL) and filtered through a plug of silica (50 mm×50 mm) using CHCl3 (50 mL) followed by CHCl3/MeOH (95:5) as eluents. Solvents from the pure fractions were removed under reduced pressure to give 4.8 g (76%) of the title compound as a light brown oil. HRMS m/z calcd for C12H19NO3 (M)+ 225.1365. found 225.1363.

Workup

customThe solvent from the filtered solution was evaporated under reduced pressure
dissolutionthe resulting residue was dissolved in CHCl3 (50 mL)
filtrationfiltered through a plug of silica (50 mm×50 mm)
customSolvents from the pure fractions were removed under reduced pressure

Sources & evidence

ORD record: ord-af1f2fbed59141de9284a075c809c2b5
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226925B2

Reaction notes

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