Triethylamine → (3-Cyanophenyl-hydroxy-methyl]-phosphonic acid dimethyl ester

HRID 45822

Reaction equation

HRID 45822 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])=[O:2].C(N(CC)CC)C.[CH3:18][O:19][P:20]([O-:23])[O:21][CH3:22]>C(OCC)(=O)C>[CH3:18][O:19][P:20]([CH:1]([C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([C:6]#[N:7])[CH:4]=1)[OH:2])(=[O:23])[O:21][CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90670m-FormylbenzonitrileHCID 21884954Dimethylphosphite

Product 1

HCID 86654332(3-Cyanophenyl-hydroxy-methyl]-phosphonic acid dimethyl esterYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-formyl-benzonitrile (10 g, 76.26 mmol), triethylamine (9.26 g, 91.05 mmol) and dimethyl-phosphite (10.91 g, 99.14 mmol) was stirred in ethyl acetate at room temperature for 2 hours. The solvent was evaporated and the residue was dissolved in ethyl acetate (50 ml), washed with a saturated ammonium chloride solution (1×50 ml), dried (Na2SO4) and the filtrate was evaporated affording the crude [(3-cyanophenyl-hydroxymethyl]-phosphonic acid dimethyl ester as a yellow solid (13.60 g, 56.43 mmol, 74%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  3. washwashed with a saturated ammonium chloride solution (1×50 ml)
  4. dry with materialdried (Na2SO4)
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-8ad35e0839e64030a4ffa510d4304690
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Linked notes

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