Hydrochloric Acid → HCID 19775798, compound

3-Cyclopentenecarboxylic acid (7.5 g, 66.9 mmole) in dry tetrahydrofuran (15 ml) was added dropwise under nitrogen to a stirred solution of lithium diisopropylamide prepared from diisopropylamine (19.7 ml, 0.14 mole) and 2.5M n-butyl lithium in hexane (56.2 ml, 0.14 mole) in dry tetrahydrofuran (150 ml) at -60° C. The resulting suspension was allowed to warm to room temperature and then stirred for a further hour, by which time a clear solution was obtained. Iodopropane (7.18 ml, 73.6 mmole) was added dropwise at -60° C., and the mixture was once again allowed to warm to room temperature and then stirred overnight. The solution was cooled to 15° C., water (10 ml) was added followed by 2N hydrochloric acid to pH 3. The organic layer was separated and the aqueous phased extracted twice with methylene chloride. The combined organic extracts were washed with saturated salt solution, dried (MgSO4) and evaporated under vacuum to give a crude product which was chromatographed on silica gel (200 g), eluting with a mixture of ethyl acetate and hexane to give 1-propyl-3-cyclopentene-carboxylic acid (7.96 g, 77%) as a hygroscopic solid.

1. customwas obtained
2. temperatureto warm to room temperature
3. stirringstirred overnight
4. temperatureThe solution was cooled to 15° C.
5. customThe organic layer was separated
6. extractionthe aqueous phased extracted twice with methylene chloride
7. washThe combined organic extracts were washed with saturated salt solution
8. dry with materialdried (MgSO4)
9. customevaporated under vacuum
10. customto give a crude product which
11. customwas chromatographed on silica gel (200 g)
12. washeluting with a mixture of ethyl acetate and hexane

ORD record

ord-79f18724ddb34d73a394828843f1d313

Source dataset

uspto-grants-1993_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05192800