Acetonitrile → 11-Carbethoxyundecyltriphenylphosphonium bromide

HRID 1089340ノート

反応式

HRID 1089340 の反応式
[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]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 235144Ethyl 11-bromoundecanoate

生成物 2

HCID 5460504PhosphoniumHCID 1906338411-Carbethoxyundecyltriphenylphosphonium bromide収率 83%

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6056a863d07a4c0f9fadc847701f12e5
出典データセット
uspto-grants-1990_10
特許番号
US04965391

反応ノート

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