Potassium Carbonate → HCID 61834257, Verbindung

HRID 63082

Reaktionsgleichung

Reaktionsgleichung von HRID 63082
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.Br[CH2:14][CH:15]1[CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CCOC(C)=O>[CH:15]1([CH2:14][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH2:17][CH2:16]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Produkt 1

HCID 61834257HCID 61834257, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 6-hydroxy-1-tetralone (2.0 g, 12.3 mmol) in ACN (30 mL) was added (bromomethyl)cyclopropane (2.0 g, 14.7 mmol) and K2CO3 (3.4 g, 24.6 mmol) at rt. The mixture was heated at 80° C. overnight. After the reaction was cooled to rt, it was diluted with EtOAc, filtered, and concentrated. The residue was purified by column chromatography (20:1 PE/EtOAc) to give 2.3 g (87%) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 0.35-0.40 (2H, m), 0.65-0.71 (2H, m), 1.25-1.32 (1H, m), 2.08-2.16 (2H, m), 2.62 (2H, t, J=6.3 Hz), 2.93 (2H, t, J=6.0 Hz), 3.87 (2H, d, J=7.2 Hz), 6.71 (1H, s), 6.83 (1H, dd, J=2.1, 8.4 Hz), 8.01 (1H, d, J=8.4 Hz).

Aufarbeitung

  1. temperatureAfter the reaction was cooled to rt
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (20:1 PE/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-5f27d48321c84bbbaa6fe4aeb2d58e56
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447045B2

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