Triphenylphosphine → (Cyclopentylmethyl)triphenylphosphonium iodide

HRID 398550ノート

反応式

HRID 398550 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 86.3%

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 (4.60 g, 21.89 mmol) and triphenylphosphine (5.74 g, 21.89 mmol) in acetonitrile (22 mL) was heated under reflux for 2 weeks. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to provide an orange solid. The orange 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 solid was allowed to air dry to afford cyclopentylmethyl triphenylphosphonium iodide (8.92 g, 86%) as a light orange 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 2 weeks
  2. concentrationconcentrated in vacuo
  3. customto provide an orange solid
  4. customThe orange 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-dd681fbd18064ed8916585d082974606
出典データセット
uspto-grants-2003_08
特許番号
US06610846B1

反応ノート

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