Reaction #321498

Reaction equation

methoxyethoxymethyl chloride

N-(3,4-dimethyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide

sodium hydride

→

colorless oil

Yield 56.4%

N-(methoxyethoxymethyl)-N-(3,4-dimethyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide

Yield 56.4%

Solvents

THF

THF

Conditions

Workup

1. 1
   TemperatureThe solution was warmed to room temperature
2. 2
   OtherEvaporation of solvent
3. 3
   workup.WAITleft an oil that
4. 4
   Extractionwas extracted into ethyl acetate
5. 5
   Washwashed with brine
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Otherevaporated

Procedure

N-(3,4-dimethyl-5-isoxazolyl)-5-bromothiophene-2-sulfonamide (680 mg, 2 mmol) in dry THF (2 ml) was added to sodium hydride (121 mg of a 60% oil dispersion, 3 mmol) in dry THF (1 ml). The resulting suspension was cooled to 0° C. and methoxyethoxymethyl chloride (334 mg, 2.68 mmol) was added dropwise via syringe. The solution was warmed to room temperature, and stirring continued overnight. Evaporation of solvent left an oil that was extracted into ethyl acetate, washed with brine, dried over magnesium sulfate and evaporated. Flash chromatography of the residue on silica gel using 10-15% ethylacetate/hexanes yielded 480 mg (56%) of a colorless oil.

Source