Hydrochloric Acid → HCID 118106659, compound

3.2 g (14.02 mmol) of diethyl 3-cyclopropylpentanedioate were dissolved in 24.7 ml of abs. THF, and, after cooling to −10° C., 25.2 ml (25.2 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. The reaction mixture was stirred at RT overnight. After cooling to 0° C., 100 ml of isopropanol were carefully added dropwise. The mixture was acidified by addition of 1 N hydrochloric acid and mixed with Celite. After filtration through Celite and washing with ethyl acetate and water, the filtrate was saturated with sodium chloride and extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→2:1). This gave 1.35 g of the target product (66.8% of theory).

1. temperatureAfter cooling to 0° C.
2. additionmixed with Celite
3. filtrationAfter filtration through Celite
4. washwashing with ethyl acetate and water
5. extractionextracted three times with ethyl acetate
6. dry with materialThe combined organic phases were dried over magnesium sulphate
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→2:1)

ORD record

ord-b92eb5611fad446189868cccbe87d615

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309198B2