Fluorene-2-carboxaldehyde → 2-vinylfluorene

HRID 436394

Reaktionsgleichung

Reaktionsgleichung von HRID 436394
[Br-].[C:2]1([C:8]([PH3+])([C:15]2C=CC=[CH:17][CH:16]=2)[C:9]2[CH:14]=CC=C[CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([Li])[CH2:23]CC.C1C2CC3C(=CC=CC=3)C=2C=CC=1C=O>C1COCC1.CCCCCC>[CH:22]([C:17]1[CH:16]=[CH:15][C:8]2[C:2]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:14][C:9]=2[CH:10]=1)=[CH2:23]

Komponenten

6

Edukt 3

HCID 34804Fluorene-2-carboxaldehydeHCID 21951224Triphenylmethyl phosphonium bromideHCID 178418339Butyllithium

Produkt 1

HCID 110416072-vinylfluorene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel2×

Versuchsvorschrift

Triphenylmethyl phosphonium bromide (36 gms/0.1 mole) in 500 milliliters of dry THF is treated under nitrogen with 90 milliliters of a 1.1 molar solution of n-butyl lithium in hexane and stirred for 2 hours. A solution of 19.4 gms. (0.1 mole) of fluorene-2-carboxaldehyde in 100 milliliters of THF is added dropwise and the final mixture refluxed for 1 1/2 hours. One liter of hexane is added to the cold solution and the precipitate filtered off. The filtrate is evaporated and the residue chromatographed on alumina (Woehlm neutral) using hexane to give 15 gms. (75% theory) of product. Recrystallization from hexane yields 2-vinylfluorene as colorless plates. The structure of the product is confirmed by nuclear magnetic resonance and elemental analysis.

Aufarbeitung

  1. filtrationthe precipitate filtered off
  2. customThe filtrate is evaporated
  3. customthe residue chromatographed on alumina (Woehlm neutral)
  4. customto give 15 gms
  5. customRecrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-10324234b1f54679ae0cd77a3b39a8ac
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04009151

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