Hydrochloric Acid → HCID 13343383, compound

Temperature

0 °C

A solution of diisopropylamine (15.4 mL, 0.11 mol) in tetrahydrofuran is cooled to 0° C., treated dropwise with a 2.04 M solution of n-butyllithium in tetrahydro-furan (51.4 mL, 0.105 mol), stirred at 0° C. for 30 minutes, treated dropwise with ethyl (isopropylthio)acetate (16.3 g, 0.1 mol), stirred at 0° C. for 1 hour, treated with methyl iodide (15.6 g, 0.11 mol), stirred at room temperature for 20 hours, and poured into an ice-water mixture (100 g) containing 15 mL of 6 N hydrochloric acid. The resulting aqueous mixture is extracted with ether. The combined organic extracts are washed sequentially with water, saturated sodium thiosulfate solution, water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a brown solution. Vacuum distillation of the brown solution gives the title product as a liquid (10.0 g) which is identified by NMR spectral analysis.

1. stirringstirred at 0° C. for 1 hour
2. stirringstirred at room temperature for 20 hours
3. extractionThe resulting aqueous mixture is extracted with ether
4. washThe combined organic extracts are washed sequentially with water, saturated sodium thiosulfate solution, water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated in vacuo
7. customto obtain a brown solution
8. distillationVacuum distillation of the brown solution

ORD record

ord-602d2a9ccfa54643b5b62f3048cb3e1c

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06359009B1