Acetonitrile → 11-Carbethoxyundecyltriphenylphosphonium bromide

HRID 1534155Notes

Reaction equation

HRID 1534155 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 The crude product
  4. customwas triturated with ether The solid
  5. filtrationwas filtered
  6. washwashed with ether

Sources & evidence

ORD record
ord-a0bae719102d42868f6a2687d56673df
Source dataset
uspto-grants-1992_02
Patent number
US05087721

Reaction notes

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