Pyridine → 9-Anthrylmethyl methacrylate

HRID 1748931

Reaktionsgleichung

[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][OH:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.N1C=CC=CC=1.[C:30](Cl)(=[O:34])[C:31]([CH3:33])=[CH2:32]>C1COCC1>[C:30]([O:16][CH2:15][C:13]1[C:12]2[C:7]([CH:6]=[C:5]3[C:14]=1[CH:1]=[CH:2][CH:3]=[CH:4]3)=[CH:8][CH:9]=[CH:10][CH:11]=2)(=[O:34])[C:31]([CH3:33])=[CH2:32]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

9-Anthracenemethanol (30 g) was dissolved in freshly distilled THF (150 mL). To the solution triethylamine (30 mL) and pyridine (20 mL) were added and the mixture was cooled down to 0° C. Then methacryloyl chloride (21 mL) was added dropwise. After the addition, ice-water bath was removed and the mixture was stirred for 1 hour. After water (75 mL) was added to the reaction flask, the solution was transferred into separatory funnel and extracted with diethyl ether (500 mL). The extract was washed with aqueous HCl (1 M, 150 mL), aqueous NaHCO3 (5%, 150 mL), and brine (150 mL), respectively. The solvent was evaporated in vacuum and recrystallized with methanol. (Product: 21 g) 1H NMR (500 MHz, CDCl3): δ 8.55 (s, 1H), 8.41 (d, J=8.9 Hz, 2H), 8.07 (d, J=8.4 Hz, 2H), 7.61 (t, J=7.7 Hz, 2H), 7.53 (t, J=7.9 Hz, 2H), 6.25 (s, 2H), 6.08 (s, 1H), 5.54 (s, 1H), 1.95 (s, 3H) ppm.

Aufarbeitung

customwas removed
additionAfter water (75 mL) was added to the reaction flask
customthe solution was transferred into separatory funnel
extractionextracted with diethyl ether (500 mL)
washThe extract was washed with aqueous HCl (1 M, 150 mL), aqueous NaHCO3 (5%, 150 mL), and brine (150 mL)
customThe solvent was evaporated in vacuum
customrecrystallized with methanol

Quellen und Nachweise

ORD-Eintrag: ord-1980f3b4a9864438b3fc817b8bcccb0a
Quelldatensatz: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09153353B2

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