Ethyl chloroformate → Dibenzyl ethoxycarbonylphosphonate

HRID 280870Notes

Reaction equation

HRID 280870 reaction equation
[Na].[CH2:2]([O:9][P:10]([O-:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Na+].C(OP([O-])OCC1C=CC=CC=1)C1C=CC=CC=1.Cl[C:40]([O:42][CH2:43][CH3:44])=[O:41]>CCOCC.C(O)C>[CH2:43]([O:42][C:40]([P:10](=[O:19])([O:9][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:41])[CH3:44]

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 5360545SodiumHCID 21904359DibenzylphosphiteHCID 23706462Sodium dibenzylphosphite

Product 1

HCID 23320149Dibenzyl ethoxycarbonylphosphonate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Ethanol (4.6 g) was added to a fine suspension of sodium metal (2.25 g) in dry ether (200 ml) under an atmosphere of nitrogen. The mixture was heated for 8 hours, after which dibenzylphosphite (25.7 g) in dry ether (50 ml) was added. After standing over-night the dibenzylphosphite sodium salt was added over a period of 2 hours to a cold solution of ethyl chloroformate (10.8 g) in ether, under an atmosphere of nitrogen. The reaction was heated at reflux for 1 hour, cooled, washed with water, a NaCl solution and dried over Na2SO4. The ether was evaporated. After evaporating and discarding components volatile at 0.01 mm and 150° C. the residue was collected (13 g).

Workup

  1. temperatureThe mixture was heated for 8 hours
  2. waitAfter standing over-night
  3. temperatureThe reaction was heated
  4. temperatureat reflux for 1 hour
  5. temperaturecooled
  6. washwashed with water
  7. dry with materiala NaCl solution and dried over Na2SO4
  8. customThe ether was evaporated
  9. customAfter evaporating
  10. customvolatile at 0.01 mm and 150° C.
  11. customwas collected (13 g)

Sources & evidence

ORD record
ord-7e0c4aaf47fa4e0ea6fd0a16267b9003
Source dataset
uspto-grants-1986_05
Patent number
US04591583

Reaction notes

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