Butylamine → (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-3-hydroxybenzylamine

HRID 1708674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1708674
Cl/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)[CH2:6][CH3:7].C(N)CCC.[C:21]([C:25]#[CH:26])([CH3:24])([CH3:23])[CH3:22]>[Cu]I.O1CCCC1>[CH3:22][C:21]([CH3:24])([CH3:23])[C:25]#[C:26]/[CH:2]=[CH:3]/[CH2:4][N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)[CH2:6][CH3:7]

Komponenten

6

Edukt 3

HCID 8007ButylamineHCID 135123,3-Dimethyl-1-butyneHCID 10376384(E)-N-(3-Chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamine

Produkt 1

HCID 10445905(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-3-hydroxybenzylamineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 30 ml of tetrahydrofuran were added 4.51 g (20 mmol) of (E)-N-(3-chloro-2-propenyl)-N-ethyl-3-hydroxybenzylamine, 190.5 mg (1 mmol) of copper (I) iodide and 324 mg (0.28 mmol) of tetrakis (triphenyiphosphine)palladium, and further, 3.95 ml (40 mmol) of n-butylamine and 2.94 ml (24 mmol) of tert-butylacetylene under ice cooling. The mixture was stirred for 20 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was subjected to silica gel chromatography (n-hexane→n-hexane/ethyl acetate=7/3). The desired fractions were put together and concentrated under reduced pressure to oil. The oil was cooled to crystallize and the crystals were suspended in cooled n-hexane. The crystals were collected by filtration and then dried to obtain 4.20 g (yield: 77%) of the above identified compound as slightly yellow crystalline powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationconcentrated under reduced pressure to oil
  3. temperatureThe oil was cooled
  4. customto crystallize
  5. filtrationThe crystals were collected by filtration
  6. customdried
  7. customto obtain 4.20 g (yield: 77%) of the

Quellen und Nachweise

ORD-Eintrag
ord-d8344a10e99a467f995cc3f3ad9b1384
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05359091

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