Iodoethane → 1H-Inden-1-one, 5-ethoxy-2,3-dihydro-

HRID 402507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402507
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH3:19]>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2)[CH3:19]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 2331475-Hydroxy-1-indanone

Produkt 1

HCID 227325581H-Inden-1-one, 5-ethoxy-2,3-dihydro-Ausbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

5-Hydroxy-1-indanone (2.5 g, 16.0 mmol) was dissolved in acetone (60 ml) and potassium carbonate (waterfree, 5.15 g, 36.9 mmol) and ethyl iodide (2.88 ml, 35.3 mmol) were added. The reaction was stirred at it under an atmosphere of nitrogene for 6 days. The mixture was filtered, the filtrate collected and the solvent evaporated at reduced pressure. Chromatography on silica (flashmaster, hex to hex/EtOAc 2/3 in 20 min, 15 min hex/EtOAc 2/3) gave the product as off-white solid (2.8 g, 99%). [1H-NMR (DMSO-d6, 600 MHz) δ 7.54 (d, 1H), 7.07 (s, 1H), 6.94 (d, 1H), 4.13 (q, 2H), 3.05-3.03 (m, 2H), 2.58-2.56 (m, 2H), 1.35 (t, 3H); LCMS RtJ=0.88 min; [M+H]+=177.2]

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe filtrate collected
  3. customthe solvent evaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ad4886f41bd34e478bb4747d9d2b0d86
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742106B2

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