Iodoethane → ethyl 2-ethyl-7-(2-methyl-4,5-diphenyl-1H-imidazol-1-yl)heptanoate
Reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([O:13][C:14](=[O:39])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:24]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:23]=[C:22]1[CH3:38])[CH3:12].I[CH2:41][CH3:42]>C1COCC1>[CH2:11]([O:13][C:14](=[O:39])[CH:15]([CH2:41][CH3:42])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:24]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:23]=[C:22]1[CH3:38])[CH3:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
(Scheme 3 (O)) This compound was obtained using the procedures as described above. The following scales and reagents were used: 7-(2-Methyl-4,5-diphenyl-imidazol-1-yl)-heptanoic acid ethyl ester (390 mg, 1 mmole), Sodium bis(trimethylsilyl)amide (1M in THF) (1.2 ml, 1.2 mmole), Iodoethane (0.4 ml, 779.8 mg, 5 mmole), anhydrous THF (10 ml). Product was obtained (100 mg, 24%). 1H NMR (CDCl3): δ0.88 (t, 3H), 1.23 (m, 4H), 1.33 (t, 3H), 1.54 (m, 4H), 1.68 (b, 1H), 2.04 (s, 1H), 2.17 (m, 1H), 2.49 (s, 3H), 3.709 (t, 2H), 4.15 (m, 2H), 7.19 (m, 3H), 7.42 (m, 3H), 7.46 (m, 4H). 13C NMR (CDCl3): δ12.0, 13.9, 14.6, 25.7, 26.6, 27.0, 30.5, 31.9, 44.0, 47.3, 60.2, 126.1, 126.7, 128.2, 128.7, 129.2, 131.3. Anal. Calcd. for C27H34N2O2: C, 77.48; H, 8.19; N, 6.69. Found: C, 77.34; N, 8.01; N, 6.56. Mass Spec: 419.32 (MH+).
Workup
- customProduct was obtained (100 mg, 24%)
Sources & evidence
- ORD record
- ord-50c5b9b50c7c4f6f87e25aff6e3397bc
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562846B2
Reaction notes
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