Sodium hydride → Triphenylphosphine

HRID 441572Notes

Reaction equation

HRID 441572 reaction equation
[H-].[Na+].[H][H].[Br-].[C:6]1([P+:12]([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)CCCCC(O)=O)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CS(C)=O>[P:12]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 178418361HCID 178418361, compound

Product 1

HCID 11776Triphenylphosphine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Under a nitrogen atmosphere a suspension of 1.49 g of NaH (80% dispersion in mineral oil) in 40 ml of DMSO was warmed to 60°-65° C., with stirring and with exclusion of humidity for 3 hours, until no more hydrogen was evolved. It was cooled to 5°-8° C. and 10.93 g of triphenyl-(4-carboxybutyl)-phosphonium bromide was added all at once. The material was kept at 15° C. and stirred until all the reagent was dissolved, giving a DMSO solution of the ylide (C6H5)3P-CH(-) -(CH2)3COO(-).

Workup

  1. temperaturewas warmed to 60°-65° C.
  2. temperatureIt was cooled to 5°-8° C.
  3. customwas kept at 15° C.
  4. dissolutionwas dissolved

Sources & evidence

ORD record
ord-e6199fa2d5634a6e96406452178ecdd6
Source dataset
uspto-grants-1977_08
Patent number
US04041064

Reaction notes

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