Imidazole → HCID 13590265, compound

HRID 1380109Notes

Reaction equation

HRID 1380109 reaction equation
O1CC1C[CH:4]([O:13][CH:14]([CH2:23][CH:24]1OC1)C1C=CC(OC)=CC=1)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1.[O:33]1CCCC1>>[OH:33][CH:23]([CH2:14][O:13][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[CH2:24][N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 8028TetrahydrofuranHCID 566290762,3-Epoxypropyl-4-methoxybenzyl ether

Product 1

HCID 13590265HCID 13590265, compound

Procedure

2,3-Epoxypropyl-4-methoxybenzyl ether (100 g, 0.515 mol) in dry tetrahydrofuran (200 ml) was treated with imidazole (44.4 g, 0.653 mol) and heated under reflux for 16 hours. The solution was filtered and the solvent was evaporated off under reduced pressure to give a brown solid which was recrystallised from 10% water-propan-1-ol to give 1-[2-hydroxy-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole as a colourless crystalline solid, m.p. 96°-98° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. filtrationThe solution was filtered
  4. customthe solvent was evaporated off under reduced pressure
  5. customto give a brown solid which
  6. customwas recrystallised from 10% water-propan-1-ol

Sources & evidence

ORD record
ord-e68f773d46644f24a9923064e22cb1a6
Source dataset
uspto-grants-1986_04
Patent number
US04579862

Reaction notes

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