HCID 10353361, Verbindung → HCID 57424364, Verbindung

HRID 604332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604332
[N+:1]([CH2:4][C:5]([C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15])=[O:6])([O-:3])=[O:2].I[CH2:17][C:18]([CH2:20]I)=[CH2:19]>CN(C)C=O.C(N(CC)C(C)C)(C)C>[CH2:17]=[C:18]1[CH2:20][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:7]2[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=2[F:15])[O:6][CH2:19]1

Komponenten

5

Edukt 2

HCID 10353361HCID 10353361, VerbindungHCID 110450293-Iodo-2-(iodomethyl)prop-1-ene

Produkt 1

HCID 57424364HCID 57424364, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 3-chloro-2-(chloromethyl)prop-1-ene (1.0 g, 8 mmol) and sodium iodide (6.6 g, 44 mmol) in acetone (60 mL) was stirred at room temperature for 20 hours, evaporated under reduced pressure and dissolved in dichloromethane (150 mL) and water (50 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to yield 3-iodo-2-(iodomethyl)prop-1-ene as a reddish oil (2.45 g). To a solution of 2-nitro-1-(2,4,5-trifluorophenyl)ethanone (110 mg, 0.5 mmol) in N,N-dimethylformamide (3 mL), N,N-diisopropylethylamine (0.20 mL) and 3-iodo-2-(iodomethyl)prop-1-ene (170 mg, 0.55 mmol) were added and the mixture was heated at 60° C. for 2.5 hours, evaporated and purified by chromatography on a Biotage Horizon® system (silica, gradient 0-30% dichloromethane in hexane) to yield 3-methylene-5-nitro-6-(2,4,5-trifluorophenyl)-3,4-dihydro-2H-pyran.

Aufarbeitung

  1. customevaporated
  2. custompurified by chromatography on a Biotage Horizon® system (silica, gradient 0-30% dichloromethane in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8dc7f0a1e8ad45eca098d5d7b763e2ef
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910596B2

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