Water → HCID 316212, compound

Temperature

40 °C

N-Valeric acid (1 g) was dissolved in 75 ml of tetrahydrofuran and treated with 2 equivalents of lithium diisopropylamide at room temperature. The solution was then heated to 40° C. for 30 minutes followed by the addition of 1.1 ml of benzyl chloride. After 1.5 hours at 40° C., the reaction mixture was cooled to room temperature, poured into 300 ml of water and extracted with diethyl ether (2×200 ml). The aqueous solution was then acidified with 1M hydrochloric acid and extracted with diethyl ether (2×300 ml). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. The residue was purified by radial chromatography (40-50% ethyl acetate in hexane, 2 mm plate) to yield 1.63 g of 2-benzylpentanoic acid (87% yield).

1. temperaturethe reaction mixture was cooled to room temperature
2. extractionextracted with diethyl ether (2×200 ml)
3. extractionextracted with diethyl ether (2×300 ml)
4. dry with materialThe combined organic extracts were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by radial chromatography (40-50% ethyl acetate in hexane, 2 mm plate)

ORD record

ord-eef8f2022f9d4b7486bbbf37edffb643

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05840729