Isopropanol → Diisopropyl 1-benzyl-2-isopropoxymethylimidazole-4,5-dicarboxylate

HRID 265195Notes

Reaction equation

HRID 265195 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]([O:15]CC)=O)=[C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:10][C:9]1([CH3:24])Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][CH:26]([CH3:28])[O-:27].[Na+].[OH:30][C:31](C1N=C(COCC)NC=1C(OCC)=O)([CH3:33])[CH3:32].[CH:48](O)(C)C>O1CCCC1>[CH2:1]([N:8]1[C:12]([C:13]([O:27][CH:26]([CH3:28])[CH3:25])=[O:15])=[C:11]([C:18]([O:20][CH:21]([CH3:22])[CH3:48])=[O:19])[N:10]=[C:9]1[CH2:24][O:30][CH:31]([CH3:33])[CH3:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3776Isopropanol2×HCID 109204432-Propanol, sodium salt (1:1)HCID 70219750Diethyl 1-benzyl-2-bromo-methylimidazole-4,5-dicarboxylateHCID 178467660HCID 178467660, compound

Product 1

HCID 19036288Diisopropyl 1-benzyl-2-isopropoxymethylimidazole-4,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.19 g of diethyl 1-benzyl-2-bromomethylimidazole-4,5-dicarboxylate [prepared as described in Preparation 42(ii)] in 20 ml of isopropanol and 25 ml of tetrahydrofuran was added dropwise to a solution of sodium isopropoxide in isopropanol (prepared from 0.77 g of sodium and 100 ml of isopropanol), and then, the resulting mixture was heated under reflux for 5 hours. The reaction solution was then treated following a procedure similar to that described in Preparation 42 (iii). The residue was purified by column chromatography through silica gel, using a 3:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.47 g of the title compound as a syrup.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. additionThe reaction solution was then treated
  4. customThe residue was purified by column chromatography through silica gel
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-657bbfbc481d4e45bfff33b9bbc848e1
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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