Methyl iodide → 1-[2-[(6-Methoxyhexyl)oxy]-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole

HRID 845475Notes

Reaction equation

HRID 845475 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]([CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[H-].[Na+].[CH3:29]I>O1CCCC1>[CH3:29][O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]([CH2:16][O:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 201311551-[2-[(6-hydroxyhexyl)oxy]-3-[(4-methoxyphenyl)methoxy]-propyl]-1H-imidazole

Product 1

HCID 201311951-[2-[(6-Methoxyhexyl)oxy]-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[2-[(6-Hydroxyhexyl)oxy]-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole (Example 23) (0.3 g, 0.00086 mol) was added to a suspension of sodium hydride (0.006 g of an 80% dispersion in oil, 0.002 mol) in dry tetrahydrofuran (5 ml) at 25° C. and the resulting slurry stirred for 1 hour at this temperature. Methyl iodide (0.284 g, 0.002 mol) was then added and the resulting suspension stirred at 25° C. overnight. The suspension was then evaporated under reduced pressure and the residue poured into dilute hydrochloric acid (6N, 20 ml) and washed with ethyl acetate (2×5 ml), the aqueous phase was then basified with solid potassium carbonate and the liberated oil extracted into ethyl acetate (10 ml), the organic phase was then dried and evaporated under reduced pressure to give the product which was purified by column chromatography (silica gel, 10% methanol in ethyl acetate) to give the title compound as a pale yellow oil.

Workup

  1. stirringthe resulting suspension stirred at 25° C. overnight
  2. customThe suspension was then evaporated under reduced pressure
  3. additionthe residue poured into dilute hydrochloric acid (6N, 20 ml)
  4. washwashed with ethyl acetate (2×5 ml)
  5. extractionthe liberated oil extracted into ethyl acetate (10 ml)
  6. customthe organic phase was then dried
  7. customevaporated under reduced pressure
  8. customto give the product which
  9. customwas purified by column chromatography (silica gel, 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-2d2a5990659b479883e2ecae859617d0
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

Loading…