Methyl iodide → Isoxazole, 5-(7-(4-(4,5-dihydro-5-(methoxymethyl)-2-oxazolyl)phenoxy)heptyl)-3-methyl-

HRID 2165410Notes

Reaction equation

HRID 2165410 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH:5]1[O:9][C:8]([C:10]2[CH:29]=[CH:28][C:13]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[O:26][N:25]=[C:24]([CH3:27])[CH:23]=3)=[CH:12][CH:11]=2)=[N:7][CH2:6]1.[CH3:30]I>O1CCCC1>[CH3:30][O:3][CH2:4][CH:5]1[O:9][C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[O:26][N:25]=[C:24]([CH3:27])[CH:23]=3)=[CH:28][CH:29]=2)=[N:7][CH2:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 52721595-Oxazolemethanol, 4,5-dihydro-2-(4-((7-(3-methyl-5-isoxazolyl)heptyl)oxy)phenyl)-

Product 1

HCID 5272161Isoxazole, 5-(7-(4-(4,5-dihydro-5-(methoxymethyl)-2-oxazolyl)phenoxy)heptyl)-3-methyl-Yield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 1.08 g of sodium hydride (60% in mineral oil) in 50 ml of dry tetrahydrofuran was added over 33 minutes a solution of 6.6 g of 5-{7-[4-(4,5-dihydro-5-hydroxymethyl-2-oxazolyl)phenoxy]heptyl}-3-methylisoxazole (Example 23). The mixture was heated at gentle reflux for one hour, then cooled to room temperature, and 4.30 g of methyl iodide in 25 ml of dry tetrahydrofuran was added over a 15 minute period. The reaction mixture was stirred overnight at room temperature, then filtered and concentrated in vacuo. The residue was washed with n-pentane and dissolved in ethyl acetate and the soluble portion isolated (6.31 g, m.p. 53°-55° C.). The latter was recrystallized from hexane to give 5.1 g of 5-{7-[4-(4,5-dihydro-5-methoxymethyl-2-oxazolyl)phenoxy]heptyl}-3-methylisoxazole, m.p. 60°-61° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat gentle reflux for one hour
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with n-pentane
  6. dissolutiondissolved in ethyl acetate
  7. customthe soluble portion isolated (6.31 g, m.p. 53°-55° C.)
  8. customThe latter was recrystallized from hexane

Sources & evidence

ORD record
ord-95fd83a1019841afaaf60921244f43a1
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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