Acetic Acid → HCID 9990911, compound

HRID 729145Notes

Reaction equation

HRID 729145 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.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 1194401-Hydroxyethyl radicalHCID 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 ofsodium 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° (extremelyexothermic). 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 withanhydrous magnesium sulphate and removed in vacuo to afford ethyl 2-cyanoethyl(tetrahydrofuran-2-yl)-phosphinate; 1H-NMR (CDCl3): δ4.15 (3 H, m), 3.90 (2 H, m), 2.72 (2 H, m, CH2CN), 2.34-1.87(6 H, m), 1.32 (3 H, 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 withanhydrous magnesium sulphate
  8. customremoved in vacuo

Sources & evidence

ORD record
ord-782c600cef184da5a88c04ee1eb8306b
Source dataset
uspto-grants-1991_09
Patent number
US05051524

Reaction notes

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