Acetonitrile → 11-Carbethoxyundecyltriphenylphosphonium bromide
Reaktionsgleichung
[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
Versuchsvorschrift
Ethyl-11-bromoundecanoate (36.0 g, 123 mmol) and acetonitrile (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
- customequipped with a reflux condenser
- temperaturethe reaction mixture was refluxed for 36 hours under anhydrous conditions
- customthe acetonitrile was removed under reduced pressure The crude product
- customwas triturated with ether The solid
- filtrationwas filtered
- washwashed with ether
Quellen und Nachweise
- ORD-Eintrag
- ord-a0bae719102d42868f6a2687d56673df
- Quelldatensatz
- uspto-grants-1992_02
- Patentnummer
- US05087721
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