Delta-Valerolactone → HCID 13105375, Verbindung

HRID 1981225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1981225
C([Li])CCC.[C:6]1([P:12](=[O:30])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:31]1(=[O:37])[O:36][CH2:35][CH2:34][CH2:33][CH2:32]1>CCCCCC.O1CCCC1>[OH:37][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([CH:13]([P:12](=[O:30])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:36]

Komponenten

6

Edukt 3

HCID 10953Delta-ValerolactoneHCID 13105374HCID 13105374, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 13105375HCID 13105375, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

1.6M n-Butyl lithium solution in hexane (56 ml) was added to a stirred solution of the phosphine oxide (31.0 g) in dry tetrahydrofuran (400 ml) at -40° to -45° C. under nitrogen. The deep orange solution was stirred for 10 minutes at -40° to -50° C., then a solution of valerolactone (9.0 g) in dry tetrahydrofuran was added. The pale solution was allowed to warm to room temperature, poured on to ice and extracted with ether. The extract was dried and evaporated and the residue was crystallised from ether-petroleum spirit to give 1-(5-hydroxypentanoyl)undecyl-diphenylphosphine oxide, m.p. 70° C.

Aufarbeitung

  1. additionpoured on to ice
  2. extractionextracted with ether
  3. customThe extract was dried
  4. customevaporated
  5. customthe residue was crystallised from ether-petroleum spirit

Quellen und Nachweise

ORD-Eintrag
ord-be69411727394e9684c9ad04f10426a6
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04513005

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