Imidazole → HCID 13590265, compound

HRID 980218Notes

Reaction equation

HRID 980218 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-103924dadb334435a82480e9dc6a250f
Source dataset
uspto-grants-1987_01
Patent number
US04636518

Reaction notes

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