Imidazole → HCID 13590265, compound

HRID 1285375Notes

Reaction equation

HRID 1285375 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, 0.725M) in dry tetrahydrofuran (200 ml) was treated with imidazole (44.4 g, 0.765M) 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 (83 g) 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-03a6d9d5754246e984d196cbf65b3fb3
Source dataset
uspto-grants-1986_01
Patent number
US04567189

Reaction notes

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