Pyridine → HCID 73184319, compound

A solution of ethyl hexa-3,5-dienoate (4.0 g, 28.6 mmol) in dry tetrahydrofuran (200 mL) was treated with a solution of lithium aluminum hydride in tetrahydrofuran (1.0 M, 28.6 mL, 28.6 mmol). The mixture was stirred at room temperature for 2 hours, and then quenched with water. The mixture was acidified with 1.0 N aqueous hydrochloric acid and extracted three times with ethyl acetate. The organic layers were combined, dried over sodium sulfate and concentrated to a yellow oil. 1H NMR (300 MHz, CDCl3) δ6.4-6.1 (m, 2H), 5.67 (m, 1H), 5.13 (d, J=17 Hz, 1H), 5.00 (d, J=11 Hz, 1H), 3.66 (t, J=6.6 Hz, 2H), 2.34 (q, J=6.6 Hz, 2H), 2.13 (broad s, 1H). The oil was dissolved in dichloromethane, cooled to 0° C. and treated with pyridine (10 mL) and p-toluenesulfonyl chloride (5.72 g, 30 mmol). The mixture was stirred for one hour, then warmed to room temperature and stirred for 3 hours. The mixture was then concentrated, and the residue was dissolved in ethyl acetate, washed sequentially with water, 1.0 N aqueous hydrochloric acid, 1.0 N aqueous sodium hydroxide, and saturated aqueous sodium chloride, then was dried over magnesium sulfate and concentrated to provide a yellow oil. This yellow oil was purified by flash column chromatography, eluting with 10% ethyl acetate/hexane, to give a colorless oil (3.84 g, 53%). 1H NMR (300 MHz, CDCl3) δ7.78 (d, J=8 Hz, 2H), 7.33 (d, J=8 Hz, 2H), 6.22 (td, J=17, 10 Hz, 1H), 6.04 (dd, J=11, 10 Hz, 1H), 5.10 (d, J=17 Hz, 1H), 5.02 (d, J=10 Hz, 1H), 4.05 (t, J=7 Hz, 2H), 2.44 (s+m, 5H).

1. customquenched with water
2. extractionextracted three times with ethyl acetate
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated to a yellow oil
5. dissolutionThe oil was dissolved in dichloromethane
6. temperaturecooled to 0° C.
7. stirringThe mixture was stirred for one hour
8. temperaturewarmed to room temperature
9. stirringstirred for 3 hours
10. concentrationThe mixture was then concentrated
11. dissolutionthe residue was dissolved in ethyl acetate
12. washwashed sequentially with water, 1.0 N aqueous hydrochloric acid, 1.0 N aqueous sodium hydroxide, and saturated aqueous sodium chloride
13. dry with materialwas dried over magnesium sulfate
14. concentrationconcentrated
15. customto provide a yellow oil
16. customThis yellow oil was purified by flash column chromatography
17. washeluting with 10% ethyl acetate/hexane

ORD record

ord-9634d1ff1d9444148659fcd0c62c4e22

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07230022B2