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

HRID 129077Notes

Reaction equation

HRID 129077 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 19372706Diethyl 1-(4-cyanophenyl)ethylphosphonate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ebd536264ca84addab3473d858f9fee5
Source dataset
uspto-grants-1995_11
Patent number
US05466687

Reaction notes

Loading…