Ethanol → HCID 22934880, compound

0.3 g (5.4 mmoles) of ethanol and 1.4 g (5.4 mmoles) of triphenylphosphine were added, at room temperature, into a solution of 1.6 g (4.5 mmoles) of 5-chloromethyl-3-(1-ethyl-5-hydroxy-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-meth-yl-2-isoxazoline dissolved in 20 ml of tetrahydrofuran. Thereto was added, with ice-cooling, 1.1 g (5.4 mmoles) of diisopropyl azodicarboxylate. The mixture was stirred for 1 hour to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water and extraction with ethyl acetate was conducted. The resulting organic layer was washed with water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography to obtain 1.5 g (yield: 86.8%) of 5-chloromethyl-3-(5-ethoxy-1-ethyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-methyl-2-isoxazoline.

1. additionThereto was added, with ice-
2. temperaturecooling
3. customto give rise
4. customto a reaction
5. customAfter the completion of the reaction
6. washThe resulting organic layer was washed with water
7. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
8. distillationThe resulting solution was subjected to reduced pressure distillation
9. customto remove the solvent
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-f5f48230c3334482a66c831d6472c8f1

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875606B2