Triphenylphosphine → HCID 21541001, Verbindung

HRID 1075844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1075844
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][Br:11])=[O:4].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[Br-:11].[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]([CH2:7][CH2:8][CH2:9][CH2:10][P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])=[O:4]

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 21540995HCID 21540995, Verbindung

Produkt 1

HCID 21541001HCID 21541001, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 1.82 g. (6.80 mmoles) of the N-trimethylacetyl-5-bromovaleramide prepared above and 2.67 g. (10.2 mmoles) of triphenylphosphine in 18 ml. of acetonitrile was heated to reflux under nitrogen for 96 hours. The solution was concentrated and the resultant solid was triturated with benzene (4x). The triturated solid was purified by silica gel column chromatography using first ethyl acetate to remove high Rf impurities then with a 9:1 mixture of methylene chloride:methanol. The salt, [4-trimethylacetylaminocarbonylbutyl]triphenylphosphonium bromide, was obtained as crystals from methylene chloride:ethyl acetate weighing 0.750 g. melting at 133.5°-138°.

Aufarbeitung

  1. temperatureto reflux under nitrogen for 96 hours
  2. concentrationThe solution was concentrated
  3. customthe resultant solid was triturated with benzene (4x)
  4. customThe triturated solid was purified by silica gel column chromatography
  5. customto remove high Rf impurities
  6. additionwith a 9:1 mixture of methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-64c9def88db5419ea21dc114c5ab8788
Quelldatensatz
uspto-grants-1976_05
Patentnummer
US03954741

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