Phenol → Ethyl 3-methyl-5-(2-oxo-3-(2-phenoxyethyl)imidazolidin-1-yl)thiophene-2-carboxylate
Reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][O:14]S(C3C=CC(C)=CC=3)(=O)=O)[C:8]2=[O:25])[S:4][C:3]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].[C:31]1(O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][O:14][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:8]2=[O:25])[S:4][C:3]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]Participants
Conditions
- Temperature
- 70 °C
Procedure
A mixture of ethyl 3-methyl-5-(2-oxo-3-(2-(tosyloxy)ethyl)imidazolidin-1-yl)thiophene-2-carboxylate (0.16 g, 0.35 mmol), phenol (0.03 g, 0.36 mmol) and potassium carbonate (0.05 g, 0.35 mmol) in N,N-dimethylformamide (3 mL) was stirred at 70° C. for 16 h, cooled to ambient temperature, and partitioned between ethyl acetate (75 mL) and water (35 mL). The organic layer was washed with brine (35 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 0-40% ethyl acetate in hexanes to afford the title compound as a colorless solid 72% yield (0.10 g): 1H NMR (300 MHz, CDCl3) δ 7.32-7.26 (m, 2H), 7.00-6.94 (m, 1H), 6.89 (d, J=7.6 Hz, 2H), 6.14 (s, 1H), 4.27 (q, J=7.1 Hz, 2H), 4.17 (t, J=4.9 Hz, 2H), 3.81 (br s, 4H), 3.72 (t, J=4.9 Hz, 2H), 2.49 (s, 3H), 1.33 (t, J=7.1 Hz, 3H): MS (ES+) m/z 375.2 (M+1).
Workup
- temperaturecooled to ambient temperature
- custompartitioned between ethyl acetate (75 mL) and water (35 mL)
- washThe organic layer was washed with brine (35 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography
- washeluted with 0-40% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-ea0dbc29de654ae79add83553fe2dd12
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063084B2
Reaction notes
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