Acetonitrile → 11-Carbethoxyundecyltriphenylphosphonium bromide

HRID 2226286노트

반응식

HRID 2226286 반응식
[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]

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 235144Ethyl 11-bromoundecanoate

생성물 2

HCID 5460504PhosphoniumHCID 1906338411-Carbethoxyundecyltriphenylphosphonium bromide수율 83%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6c1ca74fefcc4a34a52a0fe7c267be38
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05347030

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