9-Decenyl acetate → 9-Decen-1-yl (2-naphthoyl)acetate

Temperature

-78 °C

Lithium diisopropylamide (79.8 mL of a 2.0 M solution, 0.160 mol) is placed into a 250 mL three-necked round-bottomed flask fitted with a magnetic stirrer, internal thermometer, argon inlet, and addition fimnel. The flask is cooled to −78° C. 9-Decen-1-yl acetate (14.91 g, 0.075 mol) is dissolved in THF (5 mL) and the resulting solution added to the flask over 45 min. Once addition is complete, the mixture is stirred for an additional 15 min. before being treated with a solution of 2-naphthoyl chloride (13.80 g, 0.071 mol) dissolved in THF (25 mL) over 30 min. The mixture is warmed to −20° C. and stirred at that temperature for 18 h. After warming to 0° C., the mixture is quenched with 20% HCl (47 mL). The mixture is poured into a separatory fimnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2×100 mL), water (2×150 mL) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to give an orange/red oil. The oil is purified by column chromatography (elution with 2% ethyl acetate/petroleum ether) to yield a colorless oil having 1H and 13C NMR spectra consistent with the desired product.

1. customfitted with a magnetic stirrer
2. additioninternal thermometer, argon inlet, and addition fimnel
3. additionthe resulting solution added to the flask over 45 min
4. additionOnce addition
5. temperatureThe mixture is warmed to −20° C.
6. stirringstirred at that temperature for 18 h
7. temperatureAfter warming to 0° C.
8. customthe mixture is quenched with 20% HCl (47 mL)
9. additionThe mixture is poured into a separatory fimnel
10. additioncontaining ether (150 mL) and water (250 mL)
11. extractionThe aqueous layer is extracted with ether (150 mL)
12. washThe combined organic layers are washed with saturated NaHCO3 solution (2×100 mL), water (2×150 mL) and brine (150 mL)
13. dry with materialdried over MgSO4
14. filtrationfiltered
15. customThe solvent is removed by rotary evaporation
16. customto give an orange/red oil
17. customThe oil is purified by column chromatography (elution with 2% ethyl acetate/petroleum ether)
18. customto yield a colorless oil

ORD record

ord-a76a7f2df80e4797b5e7d45da2166e5c

Source dataset

uspto-grants-2001_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06184188B2