Ethanol → (6-Methoxy-indan-1-ylidene)-acetic acid ethyl ester

HRID 605527

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=O)=[CH:5][CH:4]=1.[CH3:13][CH2:14][OH:15].[H-].[Na+].C1C[O:21][CH2:20][CH2:19]1>C(OCC)C>[CH2:14]([O:15][C:20](=[O:21])[CH:19]=[C:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH2:7][CH2:8]1)[CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

6-Methoxy-indan-1-one (5.02 g, 30.95 mmol) and triethyl phosphonoacetate (15.5 mL, 78.13 mmol) was dissolved in THF (20 mL) and added slowly to a mixture of EtOH (850 μL) and NaH (60% dispersion in oil, 2.5 g). The resulting slurry was stirred at 70° C. overnight. The crude mixture was diluted with diethyl ether and washed with water and brine, dried (Na2SO4), filtered and concentrated. The product was purified by silica gel flash column chromatography (5:1 hexanes in ethyl acetate) to afford (6-Methoxy-indan-1-ylidene)-acetic acid ethyl ester (3.18 g, 47%) as a mixture (˜1:1) of E/Z isomers. 1H NMR (400 MHz, CDCl3) mixture (˜1:1) of E/Z isomers 7.37 (d, 1H) 7.27 (d, 1H), 7.09 (d, 1H), 6.99 (dd, 1H), 6.97 (d, 1H), 6.81 (dd, 1H), 6.50 (m, 1H), 6.31-6.30 (m, 1H), 4.27 (quart, 2H), 4.22 (quart, 2H), 3.87 (s, 3H), 3.86 (s, 3H), 3.60 (m, 2H), 3.36-3.33 (m, 4H), 3.05-3.02 (m, 2H), 1.37 (t, 3H), 1.31 (t, 3H).

Aufarbeitung

washwashed with water and brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe product was purified by silica gel flash column chromatography (5:1 hexanes in ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-8b8f2ff25c46466282edd2d12ad7b118
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07915253B2

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