Ethyl Acetate → Ethyl 4-(1-hydroxyethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

HRID 52912Notes

Reaction equation

HRID 52912 reaction equation
O1CCC[CH2:2]1.C[Mg]Br.[CH:9]([C:11]1[N:12]=[C:13]([CH2:58][CH2:59][CH3:60])[N:14]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[N:38]([C:39]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[N:37]=[N:36][N:35]=3)=[CH:24][CH:23]=2)[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:10].C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1>[OH:10][CH:9]([C:11]1[N:12]=[C:13]([CH2:58][CH2:59][CH3:60])[N:14]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[N:38]([C:39]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)[C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[N:37]=[N:36][N:35]=3)=[CH:26][CH:27]=2)[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 19036320Ethyl 4-formyl-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylateHCID 178420675HCID 178420675, compound

Product 1

HCID 19036137Ethyl 4-(1-hydroxyethyl)-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.0 ml of a 1M solution of methylmagnesium bromide tetrahydrofuran were added dropwise at -10° C. to a solution of 1.2 g of ethyl 4-formyl-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in step (a) above] in 5 ml of tetrahydrofuran, and the resulting mixture was stirred at a temperature between -10° C. and 0° C. for 3 hours. At the end of this time, the reaction mixture was mixed with ethyl acetate and with an aqueous solution of ammonium chloride, and the mixture was stirred at room temperature for 20 minutes. The ethyl acetate layer was then separated and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, using 1:4 and 1:2 by volume mixtures of ethyl acetate and methylene chloride as the eluent, to give 1.23 g of the title compound as a viscous oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 minutes
  2. customThe ethyl acetate layer was then separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-8db9bdba655744daa717274d089438f5
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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