Acetic Acid → HCID 9990911, compound

HRID 1612694Notes

Reaction equation

HRID 1612694 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[CH2:5]([O:7][P:8]([CH:10]1[CH2:14][CH2:13][CH2:12][O:11]1)[OH:9])[CH3:6].[O-]CC.[Na+].C(O)(=O)C>C(O)C>[C:1]([CH2:2][CH2:3][P:8]([CH:10]1[CH2:14][CH2:13][CH2:12][O:11]1)(=[O:9])[O:7][CH2:5][CH3:6])#[N:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7855AcrylonitrileHCID 2723922Sodium ethoxideHCID 53872425HCID 53872425, compound

Product 1

HCID 9990911HCID 9990911, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.68 g of acrylonitrile and 2.11 g of tetrahydrofuran-2-yl phosphonous acid ethyl ester in 5 ml of absolute ethanol is cooled to 0° under argon and treated, dropwise, with an ethanolic solution of sodium ethoxide (from 0.15 g of sodium metal and 15 ml of absolute ethanol) at such a rate so that the temperature does not exceed 5° (extremely exothermic). After the addition is completed the reaction mixture is stirred at room temperature for 30 minutes and 0.4 g of glacial acetic acid are added. The solvent is removed in vacuo and the residue partitioned between dichloromethane water. The organic layer is dried with anhydrous magnesium sulphate and removed in vacuo to afford ethyl 2-cyanoethyl(tetrahydrofuran-2-yl)-phosphinate; 1H-NMR (CDCl3): δ4.15 (3H, m), 3.90 (2H, m), 2.72 (2H, m, CH2CN), 2.34-1.87 (6H, m), 1.32 (3H, m, CH3).

Workup

  1. temperatureis cooled to 0° under argon
  2. additiontreated
  3. customdoes not exceed 5°
  4. additionAfter the addition
  5. customThe solvent is removed in vacuo
  6. customthe residue partitioned between dichloromethane water
  7. dry with materialThe organic layer is dried with anhydrous magnesium sulphate
  8. customremoved in vacuo

Sources & evidence

ORD record
ord-fa195c8c107245a5b7a940e380df8a78
Source dataset
uspto-grants-1993_03
Patent number
US05190933

Reaction notes

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