Triphenylphosphine → Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetate

HRID 1081280Notes

Reaction equation

HRID 1081280 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1>[C:26]1([P:19](=[CH:2][C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 62576Benzyl bromoacetate

Product 1

HCID 3862746Benzyl 2-(triphenyl-lambda5-phosphanylidene)acetateYield 41%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 22.9 g quantity of benzyl bromoacetate was dissolved in 100 ml of dry benzene. A 26.2 g quantity of triphenylphosphine was added thereto at room temperature and stirred overnight. The precipitated solids were collected by filtration, washed with benzene and dissolved in 250 ml of dichloromethane. A 14 ml quantity of triethylamine was added with ice-cooling and stirred with ice-cooling for 30 minutes and at room temperature for a further 30 minutes. The reaction mixture was transferred to a separating funnel, washed with water and dried over magnesium sulfate. The solvent was distilled off and diethyl ether was added to the residue. The resulting precipitate was collected by filtration to provide the title compound as white crystals (yield 41%).

Workup

  1. filtrationThe precipitated solids were collected by filtration
  2. washwashed with benzene
  3. dissolutiondissolved in 250 ml of dichloromethane
  4. additionA 14 ml quantity of triethylamine was added with ice-
  5. temperaturecooling
  6. stirringstirred with ice-
  7. temperaturecooling for 30 minutes and at room temperature for a further 30 minutes
  8. customThe reaction mixture was transferred to a separating funnel
  9. washwashed with water
  10. dry with materialdried over magnesium sulfate
  11. distillationThe solvent was distilled off
  12. additiondiethyl ether was added to the residue
  13. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-628a9047eecc46f0b5d44a9999e5bfb5
Source dataset
uspto-grants-1996_12
Patent number
US05585373

Reaction notes

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