Acetic Anhydride → Diethyl 2-acetylaminoethylphosphonate

HRID 2396909Notes

Reaction equation

HRID 2396909 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-df32361a083e44c8b73a3365e6fc906c
Source dataset
uspto-grants-1996_02
Patent number
US05495023

Reaction notes

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