Water → HCID 22117537, Verbindung

HRID 1275795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1275795
[C-:1]#[CH:2].[Li+].C(N)CN.Br[C:9]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2.O>CN(P(N(C)C)(N(C)C)=O)C.CCOCC>[C:1]([C:9]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)#[CH:2]

Komponenten

6

Edukt 3

HCID 962WaterHCID 2316249-Bromo-9-phenylfluoreneHCID 2724010Lithium acetylide-ethylenediamine (1:1)

Produkt 1

HCID 22117537HCID 22117537, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel2×

Versuchsvorschrift

Lithium acetylenide-ethylenediamine (10 mmol) is added to a dry flask under argon, diluted with 5 mL of HMPA, and cooled to between 0 and 5° C. with stirring. A solution of 8 mmol of 9-bromo-9-phenylfluorene dissolved in 4 mL of HMPA is added slowly to the reaction flask. The reaction mixture is warmed to room temperature and, after 2 h, 25 mL of water is slowly added. The mixture is taken up in 100 mL of ether and washed with 20mL of H2O, 20 mL of brine, dried (Na2SO4) and concentrated. The product is purified by chromatography over SiO2 using EtOAc/hexanes (2/98) as eluent. (Smith, W. N.; Beumel, O. F., Preparation of Alkynes with Dialkynes by reaction of monohalo- and dihaloalkanes with lithium acetylenide-ethylenediamine complex., Synthesis, 1974, 441-442.)

Aufarbeitung

  1. temperaturecooled to between 0 and 5° C.
  2. additionis added slowly to the reaction flask
  3. washwashed with 20mL of H2O, 20 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe product is purified by chromatography over SiO2
  7. custom, Preparation of Alkynes with Dialkynes
  8. custom, Synthesis, 1974, 441-442

Quellen und Nachweise

ORD-Eintrag
ord-4c246467f63049019e2974f0045eb015
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162824

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