Hydrochloric Acid → HCID 86646136, compound

Temperature

-78 °C

Dimethyl sulfoxide (18.20 mL, 256.4 mmol) was added dropwise over 15 minutes to a dichloromethane (280 mL) solution of oxalic acid chloride (16.90 g, 133.1 mmol) cooled to −78° C., and the mixture was then stirred at −78° C. for 25 minutes. Subsequently, a dichloromethane (75 mL) solution of 2-sec-butylpent-4-en-1-ol (12.20 g, 85.8 mmol) was added dropwise thereto over 30 minutes, and the mixture was stirred at −78° C. for 1 hour. Triethylamine (60.80 g, 600.8 mmol) was added dropwise thereto over 5 minutes, and the mixture was then stirred at room temperature for 2 hours. The mixture was neutralized with 2 N hydrochloric acid (310 mL). The organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain a yellow oil substance as a mixture containing the compound of interest. This compound was used in the next reaction without being further purified.

1. waitover 30 minutes
2. stirringthe mixture was stirred at −78° C. for 1 hour
3. waitover 5 minutes
4. stirringthe mixture was then stirred at room temperature for 2 hours
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. distillationThen, the solvent was distilled off under reduced pressure
7. customto obtain a yellow oil substance as a mixture
8. additioncontaining the compound of interest
9. customThis compound was used in the next reaction

ORD record

ord-ced14297815c424a9d8e3c5f6a286f55

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2