Dimethyl Sulfoxide → HCID 21221318, compound

Temperature

-70 °C

To a solution of oxalyl chloride (1.26 ml) in methylene chloride (30 ml) at -70° C., a solution of dimethylsulfoxide (2.11 ml) in methylene chloride (3.0 ml) was added dropwise. To the obtained solution, a solution of methyl 3-(4-hydroxybutyl)phenoxyacetate (1.94 g) in methylene chloride (8.0 ml) was added dropwise. Triethylamine (6.9 ml) was added dropwise thereto while the reaction temperature was maintained at -70° C. The reaction mixture was warmed slowly to -40° C. over a 30 min period and then quenched by addition of a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted with ether. The extract was washed with a saturated aqueous solution of ammonium chloride and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2) to give the title compound (1.41 g) having the following physical data.

1. temperatureThe reaction mixture was warmed slowly to -40° C. over a 30 min period
2. customquenched by addition of a saturated aqueous solution of ammonium chloride
3. extractionThe reaction mixture was extracted with ether
4. washThe extract was washed with a saturated aqueous solution of ammonium chloride
5. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
6. customevaporated
7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2)

ORD record

ord-21021df3aff140d194a6b25fb200d8c8

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05703099