Propargyl bromide → HCID 15086767, Verbindung

HRID 1534544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534544
[CH3:1][C:2]([Si:5]([CH3:14])([CH3:13])[O:6][C@H:7]1[CH2:11][CH2:10][NH:9][C:8]1=[O:12])([CH3:4])[CH3:3].[H-].[Na+].[CH2:17](Br)[C:18]#[CH:19]>O1CCCC1.C1(C)C=CC=CC=1.ClCCl>[CH3:4][C:2]([Si:5]([CH3:14])([CH3:13])[O:6][C@H:7]1[CH2:11][CH2:10][N:9]([CH2:19][C:18]#[CH:17])[C:8]1=[O:12])([CH3:1])[CH3:3]

Komponenten

7

Edukt 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 10584804(S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-one

Produkt 1

HCID 15086767HCID 15086767, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In one portion, 11.6 g of (S)-3-[[(1,1-dimethyl-ethyl)dimethylsilyl]oxy]-2-pyrrolidinone was added to a suspension of 2.35 g of 60% sodium hydride in mineral oil in 400 ml of tetrahydrofuran which was cooled to 0° C. The resulting solution was stirred at room temperature until solution was complete, then recooled to 0° C. An 80% solution of propargyl bromide in toluene (8.5 ml) was added and the resulting solution was stirred overnight. The solution was diluted with dichloromethane washed with water, dried and concentrated in vacuo. The residue was purified by chromatography (silica gel), giving (S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinone, [α]D26 =-44° (dichloromethane); mp 35°-36° C.

Aufarbeitung

  1. customrecooled to 0° C
  2. stirringthe resulting solution was stirred overnight
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-2887ad1162ba40fba438de0193d0cc25
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05089518

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