Methyl iodide → Diethyl 1-(4-cyanophenyl)ethylphosphonate

HRID 129077ノート

反応式

HRID 129077 の反応式
[CH2:1]([Li])CCC.[C:6]([C:8]1[CH:22]=[CH:21][C:11]([CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])=[CH:10][CH:9]=1)#[N:7].CI>CCCCCC.O1CCCC1>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([CH:12]([P:13](=[O:20])([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19])[CH3:1])=[CH:21][CH:22]=1)#[N:7]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 241438Diethyl (4-Cyanobenzyl)phosphonateHCID 178418339Butyllithium

生成物 1

HCID 19372706Diethyl 1-(4-cyanophenyl)ethylphosphonate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-40 °C

実験手順

18.7 ml of a 1.6M solution of n-butyllithium in n-hexane are added dropwise with stirring at -50° C. to a solution of 7.5 g of diethyl 4-cyanobenzylphosphonate in 60 ml of tetrahydrofuran, the mixture is subsequently stirred at -40° C. for 25 minutes and 4.7 g of methyl iodide in 20 ml of tetrahydrofuran are then added dropwise at -40° C. After stirring overnight at ambient temperature, the mixture is evaporated down, the residue is taken up in ethyl acetate and washed with water, and the organic phase is dried and evaporated down. After purification by column chromatography on Silica gel (petroleum ether/2-propanol=6:1 to 2:1, v/v), 5.7 g of the title compound are obtained as a colourless oil. Rf value: 0.52 (Silica gel, petroleum ether/2-propanol=3:1, v/v).

後処理

  1. stirringAfter stirring overnight at ambient temperature
  2. customthe mixture is evaporated down
  3. washwashed with water
  4. customthe organic phase is dried
  5. customevaporated down
  6. customAfter purification by column chromatography on Silica gel (petroleum ether/2-propanol=6:1 to 2:1

出典と根拠

ORDレコード
ord-ebd536264ca84addab3473d858f9fee5
出典データセット
uspto-grants-1995_11
特許番号
US05466687

反応ノート

読み込み中…