Methyl iodide → 5-{5-[2,6-Dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-(methoxymethyl)isoxazole

HRID 2165433Notes

Reaction equation

HRID 2165433 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]2[O:22][CH2:23][CH2:24][N:25]=2)[CH:18]=[C:17]([Cl:26])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH2:15][OH:16])[CH:11]=1.[H-].[Na+].[H][H].[CH3:31]I>O1CCCC1.CCOCC>[Cl:26][C:17]1[CH:18]=[C:19]([C:21]2[O:22][CH2:23][CH2:24][N:25]=2)[CH:20]=[C:2]([Cl:1])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH2:15][O:16][CH3:31])[CH:11]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 200641365-{5-[2,6-Dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-isoxazolemethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 200641005-{5-[2,6-Dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-(methoxymethyl)isoxazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.8 g of 5-{5-[2,6-dichloro-4-(4,5-dihydro-2-oxazolyl)phenoxy]pentyl}-3-isoxazolemethanol (Example 116) in 100 ml of dry tetrahydrofuran was added 0.45 g of sodium hydride. After hydrogen evolution had ceased, the solution was cooled in an ice-bath and 1.1 ml of methyl iodide was added. The reaction mixture was stirred at room temperature for 48 hrs, then diluted with ether and washed well with water. Evaporation of the solvent and chromatography provided 3.1 g of the product as a viscous yellow oil.

Workup

  1. temperaturethe solution was cooled in an ice-bath
  2. washwashed well with water
  3. customEvaporation of the solvent and chromatography

Sources & evidence

ORD record
ord-7b59cc9c13994e77a7b216e958479b03
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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