Acetonitrile → 11-Carbethoxyundecyltriphenylphosphonium bromide

HRID 1089340Notes

Reaction equation

HRID 1089340 reaction equation
[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]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 235144Ethyl 11-bromoundecanoate

Product 2

HCID 5460504PhosphoniumHCID 1906338411-Carbethoxyundecyltriphenylphosphonium bromideYield 83%

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6056a863d07a4c0f9fadc847701f12e5
Source dataset
uspto-grants-1990_10
Patent number
US04965391

Reaction notes

Loading…