Pentane → 2-[(4-methoxyphenyl)methoxy]-3-[(4-methoxyphenyl)methoxylpropyl]-1H-imidazole

HRID 980219Notes

Reaction equation

HRID 980219 reaction equation
O[CH:2]([CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[H-].[Na+].CCCCC.[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Cl)=[CH:31][CH:30]=1.[O:37]1CCCC1>>[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][O:37][CH:5]2[N:4]([CH2:3][CH2:2][CH2:9][O:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[CH:8]=[CH:7][NH:6]2)=[CH:31][CH:30]=1

Participants

6

Reactant 5

HCID 8003PentaneHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 13590265HCID 13590265, compound

Product 1

HCID 1317150132-[(4-methoxyphenyl)methoxy]-3-[(4-methoxyphenyl)methoxylpropyl]-1H-imidazole

Procedure

A solution of 1-[2-hydroxy-3-[(4-metoxyphenyl)methoxy]propyl]-1H-imidazole (206 g, 0.79M) in dry tetrahydrofuran (3700 ml) was added dropwise to a stirred slurry of sodium hydride (38 g of a 60% dispersion in oil, 0.95M; prewashed with pentane) in dry tetrahydrofuran (200 ml) at below 5° C. and under a gentle stream of dry nitrogen. The resulting mixture was stirred at room temperature for 1 hour and 4-methoxybenzyl chloride (123.2 g, 0.79M) in dry tetrahydrofuran (100 ml) was added. The resulting mixture was stirred at room temperature, protected from light, for 3 days.

Workup

  1. customat below 5° C.
  2. stirringThe resulting mixture was stirred at room temperature
  3. customfor 3 days

Sources & evidence

ORD record
ord-b0fcf56f52d940bc92a435d2ff3764d5
Source dataset
uspto-grants-1987_01
Patent number
US04636518

Reaction notes

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