Ethyl cyclooctylideneacetate → 4744-93-8

To a solution of ethyl cyclooctylideneacetate (969 mg) in ethanol (40 mL) was added 10% palladium-carbon (60 mg). The solution was stirred under hydrogen atmosphere at room temperature for 64 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. To a solution of the resulting residue (920 mg) in diethyl ether (40 mL) was added lithium aluminum hydride (132 mg) under ice cooling. The solution was stirred under ice cooling for 30 minutes and then water (0.13 mL), and a 15% aqueous sodium hydroxide solution (0.13 mL) were successively added thereto. The solution was stirred at room temperature for 15 minutes, to which water (0.39 mL) was then added. The solution was stirred for additional 30 minutes, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=2:1) to give the title compound (680 mg).

1. filtrationThe catalyst was filtered off
2. concentrationthe filtrate was concentrated under reduced pressure
3. additionTo a solution of the resulting residue (920 mg) in diethyl ether (40 mL) was added lithium aluminum hydride (132 mg) under ice cooling
4. stirringThe solution was stirred under ice cooling for 30 minutes
5. additionwater (0.13 mL), and a 15% aqueous sodium hydroxide solution (0.13 mL) were successively added
6. stirringThe solution was stirred at room temperature for 15 minutes, to which water (0.39 mL)
7. additionwas then added
8. stirringThe solution was stirred for additional 30 minutes
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=2:1)

ORD record

ord-f47121f6cef4481faea4cba8e65e9d5b

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375115B2