Acetic Anhydride → Diethyl 2-acetylaminoethylphosphonate

HRID 2295013Notes

Reaction equation

HRID 2295013 reaction equation
[NH2:1][CH2:2][CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>ClCCl.[Cl-].[Na+].O>[C:19]([NH:1][CH2:2][CH2:3][P:4](=[O:11])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10])(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2733596Diethyl (2-aminoethyl)phosphonate

Product 1

HCID 23263408Diethyl 2-acetylaminoethylphosphonateYield 93.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of diethyl 2-aminoethylphosphonate (10.5 g), triethylamine (7.0 g) in dichloromethane (200 ml) at 0° C. was added dropwise acetic anhydride (7.1 g). After 20 hours at room temperature, the reaction mixture was diluted with brine, made basic with 5% aqueous potassium carbonate, and extracted twice with dichloromethane. The extract was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (5% methanol in chloroform) to give (12.1 g) of diethyl 2-acetylaminoethylphosphonate as an oil.

Workup

  1. extractionextracted twice with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel (5% methanol in chloroform)

Sources & evidence

ORD record
ord-925c5f2df7ee49a484feb63d07a6ca33
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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