Diethyl vinylphosphonate → 2-Benzyl-3-phenyl-5-diethoxyphosphinylisoxazolidine

HRID 2248027

Reaction equation

HRID 2248027 reaction equation
[CH:1](=[N+:8]([O-:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]([P:19](=[O:26])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH2:18]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:18][CH:17]([P:19]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:26])[O:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69629Diethyl vinylphosphonateHCID 305634Benzenemethanamine,N-(phenylmethylene)-, N-oxide

Product 1

HCID 151807642-Benzyl-3-phenyl-5-diethoxyphosphinylisoxazolidineYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.11 g (10 mmol) of N-benzylidenebenzylamine N-oxide and 1.64 g (10 mmol) of diethyl vinylphosphonate in 30 ml of toluene under a nitrogen blanket is heated at reflux temperature for 5 days. The solvent is removed under reduced pressure to give 4.45 g of crude product which is then purified by preparative HPLC (Waters Prep 500A, silica gel, 3:2 heptane:ethyl acetate eluent) to give 1.15 g (31% yield) of a caramel-colored liquid.

Workup

  1. temperatureat reflux temperature for 5 days
  2. customThe solvent is removed under reduced pressure
  3. customto give 4.45 g of crude product which
  4. customis then purified by preparative HPLC (Waters Prep 500A, silica gel, 3:2 heptane:ethyl acetate eluent)

Sources & evidence

ORD record
ord-93c488ed1b7f4e3497bd60dc7648681d
Source dataset
uspto-grants-1991_08
Patent number
US05037867

Linked notes

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