Triphenylphosphine → (Cyclopentylmethyl)triphenylphosphonium iodide

HRID 398587ノート

反応式

HRID 398587 の反応式
[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

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 2762531(Iodomethyl)cyclopentane

生成物 1

HCID 22315319(Cyclopentylmethyl)triphenylphosphonium iodide収率 92%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3fe18c73b81a4885b91fb9b12be734cc
出典データセット
uspto-grants-2003_08
特許番号
US06610846B1

反応ノート

読み込み中…