Hydrochloric Acid → HCID 86646140, compound

Temperature

-78 °C

Dimethyl sulfoxide (4.82 mL, 67.9 mmol) was added dropwise over 15 minutes to a dichloromethane (75 mL) solution of oxalic acid chloride (4.47 g, 35.2 mmol) cooled to −78° C., and the mixture was then stirred at −78° C. for 30 minutes. Subsequently, a dichloromethane (20 mL) solution of 2-cyclopentylpent-4-en-1-ol (3.50 g, 22.7 mmol) was added dropwise thereto over 15 minutes, and the mixture was stirred at −78° C. for 45 minutes. Triethylamine (16.11 g, 159.3 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 1 N hydrochloric acid (160 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 15 minutes
2. stirringthe mixture was stirred at −78° C. for 45 minutes
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-3d2fde207dad423c95c3c1b20d6baf6c

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2