Acetonitrile → 11-Carbethoxyundecyltriphenylphosphonium bromide

HRID 2226286Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226286
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][Br:15])[CH3:2].[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:36](#N)C>>[PH4+:23].[Br-:15].[C:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:36][P+:23]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([O:3][CH2:1][CH3:2])=[O:16]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 235144Ethyl 11-bromoundecanoate

Produkt 2

HCID 5460504PhosphoniumHCID 1906338411-Carbethoxyundecyltriphenylphosphonium bromideAusbeute 83 %

Versuchsvorschrift

Ethyl-11-bromoundecanoate (36.0 g, 123 mmol) and acetonitriie (200 ml) were placed in a flame-dried three-neck 500 ml round-bottomed flask equipped with a reflux condenser. Triphenyl phosphine (35.5 g, 135 mmol) was added to the solution and the reaction mixture was refluxed for 36 hours under anhydrous conditions. After the reaction mixture had cooled to room temperature, the acetonitrile was removed under reduced pressure. The crude product was triturated with ether. The solid was filtered and washed with ether to yield a pure compound 3, 11-carbethoxyundecyltriphenylphosphonium bromide (56.69 g, 83% yield).

Aufarbeitung

  1. customequipped with a reflux condenser
  2. temperaturethe reaction mixture was refluxed for 36 hours under anhydrous conditions
  3. customthe acetonitrile was removed under reduced pressure
  4. customThe crude product was triturated with ether
  5. filtrationThe solid was filtered
  6. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-6c1ca74fefcc4a34a52a0fe7c267be38
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05347030

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