Isopropenyl acetate → 1-(1-methyl-1H-indol-4-yl)propan-2-one

HRID 488622

Reaktionsgleichung

Reaktionsgleichung von HRID 488622
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:11].C([O:15][C:16]([CH3:18])=[CH2:17])(=O)C.C[O-].C([Sn+](CCCC)CCCC)CCC.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1>C1(C)C=CC=CC=1>[CH3:11][N:6]1[C:7]2[C:3](=[C:2]([CH2:17][C:16]([CH3:18])=[O:15])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Komponenten

6

Edukt 4

HCID 7916Isopropenyl acetateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 11964040Methoxytri-n-butylstannaneHCID 130487594-Chloro-1-methyl-1H-indole

Produkt 1

HCID 222704771-(1-methyl-1H-indol-4-yl)propan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 0.852 g (5.14 mmol) of 4-chloro-1-methylindole in 15 mL dry toluene, 0.85 mL (7.73 mmol) isopropenyl acetate and 2.3 mL (8 mmol) tributyltin methoxide were added. The solution was heated to 100° C. After 15 min 0.24 g (0.61 mmol) 2-dicyclohexylphospino-2′-(N,N-dimethylamino)biphenyl and 0.14 g (0.153 mmol) tris(dibenzylidineacetone)dipalladium were added and heating was continued. After 2 h the solution was cooled, filtered through a pad of CELITE diatomaceous earth and the filtrate was concentrated to ca. 5 mL. This solution was purified on a silica column using a gradient of 5-20% EtOAc/hexane to obtain the title compound. 1H NMR: (500 MHz, CDCl3): δ 2.14 (s, 3H), 3.84 (s, 3H), 3.97 (s, 2H), 6.51 (d, 1H), 7-7.3 (m, 4H).

Aufarbeitung

  1. temperatureheating
  2. temperatureAfter 2 h the solution was cooled
  3. filtrationfiltered through a pad of CELITE diatomaceous earth
  4. concentrationthe filtrate was concentrated to ca. 5 mL
  5. customThis solution was purified on a silica column

Quellen und Nachweise

ORD-Eintrag
ord-c1632b9b5df64b979cf8905f7b3a1df2
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06972295B2

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