Triphenylphosphine → (Cyclopentylmethyl)triphenylphosphonium iodide

HRID 398587노트

반응식

HRID 398587 반응식
[I:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:8]1([P:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(#N)C>[I-:1].[CH:3]1([CH2:2][P+:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

참가 물질

4

반응물 2

HCID 11776TriphenylphosphineHCID 2762531(Iodomethyl)cyclopentane

생성물 1

HCID 22315319(Cyclopentylmethyl)triphenylphosphonium iodide수율 92%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
25 °C

실험 절차

A solution of iodomethylcyclopentane (129.38 g, 0.616 mol) and triphenylphosphine (161.54 g, 0.616 mol) in acetonitrile (308 mL) was heated under reflux for 9 d. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to provide a solid. The solid was triturated with diethyl ether and then filtered. The solid was washed well with diethyl ether until the washings showed the absence of iodomethylcyclopentane and triphenylphosphine by thin layer chromatography. The resulting solid was allowed to air dry to afford cyclopentylmethyl triphenylphosphonium iodide (266.92 g, 92%) as a light yellow solid: mp 195-198° C.; FAB-HRMS m/e calcd for C24H26P (M+H)+ 345.1772, found 345.1784.

후처리

  1. temperatureunder reflux for 9 d
  2. concentrationconcentrated in vacuo
  3. customto provide a solid
  4. customThe solid was triturated with diethyl ether
  5. filtrationfiltered
  6. washThe solid was washed well with diethyl ether until the washings
  7. customto air dry

출처 및 근거

ORD 기록
ord-3fe18c73b81a4885b91fb9b12be734cc
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610846B1

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