tert-Butanol → 1-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-(2-methoxyethoxymethoxymethyl)imidazole

HRID 653906Notes

Reaction equation

HRID 653906 reaction equation
C([Li])CCC.CCCCCC.C(O)(C)(C)C.[C:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:34]2[C:38]([CH2:39][OH:40])=[C:37]([Cl:41])[N:36]=[C:35]2[CH2:42][CH2:43][CH2:44][CH3:45])=[CH:29][CH:28]=1)([O:19][CH3:20])=[O:18].[CH3:46][O:47][CH2:48][CH2:49][O:50][CH2:51]Cl>O1CCCC1.C(OCC)C>[C:17]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:34]2[C:38]([CH2:39][O:40][CH2:46][O:47][CH2:48][CH2:49][O:50][CH3:51])=[C:37]([Cl:41])[N:36]=[C:35]2[CH2:42][CH2:43][CH2:44][CH3:45])=[CH:29][CH:28]=1)([O:19][CH3:20])=[O:18]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 110041921-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazoleHCID 178418244HCID 178418244, compound

Product 1

HCID 156980881-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-(2-methoxyethoxymethoxymethyl)imidazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7.50 mL of 1.6M n-butyllithium/hexane in 50 mL of tetrahydrofuran at 0° was added dropwise 1.50 mL of t-butanol. To this solution was added 4.52 g of 1-[(2'-carbomethoxybiphenyl-4-yl)-methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole followed by 1.50 ml of 2-methoxyethoxymethyl chloride. The resulting solution was stirred at 25° for 16 hours. The mixture was diluted with diethyl ether, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography afforded 3.50 g of 1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-(2-methoxyethoxymethoxymethyl)imidazole. NMR (200 MHz, CDCl3) δ 7.83 (d, 1H); 7.52 (t, 1H); 7.40 (t, 1H), 7.28 (m, 3H); 7.00 (d, 1H); 5.19 (s, 2H); 4.68 (s, 2H); 4.48 (s, 2H); 3.67 (m, 2H); 3.64 (s, 3H); 3.54 (m, 2H); 3.37 (s, 3H); 2.58 (t, 2H); 1.67 (quint., 2H); 1.34 (sext., 2H); 0.88 (t, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9990aea15658479b868040d8a5b1dcd3
Source dataset
uspto-grants-1992_07
Patent number
US05128355

Reaction notes

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