tert-Butyl 5-oxo-5,6-dihydropyridine-1(2H)-carboxylate Chemical Properties

Boiling point:

299.2±39.0 °C(Predicted)

Density 

1.130±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

-1.95±0.20(Predicted)

Appearance

Light yellow to yellow Solid

tert-Butyl 5-oxo-5,6-dihydropyridine-1(2H)-carboxylate Usage And Synthesis

Uses

tert-Butyl 3-Oxo-3,6-dihydropyridine-1(2H)-carboxylate acts as a reagent for the preparation of ω-alkoxy enones and α-amino enones from unsaturated alcoholss or unsaturatedd amines via intermediate phosphoranes and subsequent ring-closing metathesis.

Synthesis

(Step 8) tert-butyl 5-hydroxy-5,6-dihydropyridine-1(2H)-carboxylate (350 mg, 1.76 mmol) was dissolved in dichloromethane (12 mL) and Dess-Martin oxidizer (1.5 g, 3.52 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours and then filtered. The filtrate was washed with saturated aqueous sodium carbonate (50 mL) and subsequently concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 2:1, v/v) to afford the target compound tert-butyl 5-oxo-5,6-dihydropyridine-1(2H)-carboxylate as a colorless oil (340 mg, 98% yield).LC-MS (ESI, cationic mode) m/z: 142 [(M+H)+ - C4H8], 220 [M+ Na]+; 1H NMR (400 MHz, CDCl3) δ (ppm): 1.48 (s, 9H), 4.11 (s, 2H), 4.24 (s, 2H), 6.16-6.20 (m, 1H), 7.04 (s, 1H).

References

[1] Patent: WO2013/138210, 2013, A1. Location in patent: Paragraph 0248
[2] Patent: WO2017/181117, 2017, A1. Location in patent: Page/Page column 240
[3] Patent: US2011/53925, 2011, A1. Location in patent: Page/Page column 23
[4] Patent: WO2012/25155, 2012, A1. Location in patent: Page/Page column 41
[5] Synlett, 2007, # 5, p. 741 - 744

tert-Butyl 5-oxo-5,6-dihydropyridine-1(2H)-carboxylate(156496-89-8)Related Product Information

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