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

HRID 129077노트

반응식

HRID 129077 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 19372706Diethyl 1-(4-cyanophenyl)ethylphosphonate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ebd536264ca84addab3473d858f9fee5
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466687

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