Propargyl alcohol → (E)-6,6-dimethyl-4-hepten-2-yn-1-ol

HRID 1464782

Reaktionsgleichung

Reaktionsgleichung von HRID 1464782
I/[CH:2]=[CH:3]/[C:4]([CH3:7])([CH3:6])[CH3:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N)CCC.[CH2:32]([OH:35])[C:33]#[CH:34]>O1CCCC1.[Cu]I.[Pd](Cl)Cl.C(OCC)(=O)C.O>[CH3:5][C:4]([CH3:7])([CH3:6])/[CH:3]=[CH:2]/[C:34]#[C:33][CH2:32][OH:35]

Komponenten

10

Edukt 4

HCID 7859Propargyl alcoholHCID 8007ButylamineHCID 11776TriphenylphosphineHCID 11063689(E)-1-iodo-3,3-dimethylbut-1-ene

Produkt 1

HCID 19917005(E)-6,6-dimethyl-4-hepten-2-yn-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24290Palladium ChlorideKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.63 g of (E)-1- iodo-3,3-dimethyl-1-butene [see J. Org. Chem., 43, 4424 (1978)] was dissolved in 10 ml of tetrahydrofuran, and 31 mg of triphenylphosphine, 29 mg of copper(I) iodide, 11 mg of palladium chloride, 1.5 ml of n-butylamine and 0.35 ml of propargyl alcohol were added. The mixture was stirred overnight at room temperature, and then water and ethyl acetate were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1] to give 0.27 g of the captioned compound as a pale brown oil.

Aufarbeitung

  1. customThe organic layer separated
  2. customthe product was purified by silica gel column chromatography [hexane/ethyl acetate=2/1]

Quellen und Nachweise

ORD-Eintrag
ord-8bfc60aedb7d4839b58de804983eda20
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05306728

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