Triphenylphosphine → 2-Propenal, 3-(1-naphthalenyl)-, (E)-

HRID 1743957Notes

Reaction equation

HRID 1743957 reaction equation
[C:1]1([CH:11]=[CH:12][C:13](Cl)=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(C)=O>[C:1]1([CH:11]=[CH:12][CH:13]=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 534112803-(Naphthalen-1-yl)prop-2-enoyl chloride

Product 1

HCID 6024602-Propenal, 3-(1-naphthalenyl)-, (E)-Yield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 3-(1-naphthalenyl)-2-propenoyl chloride (2.5 g, 0.012 mol) and 6.03 g (0.023 mol) of triphenyl phosphine in 50 ml of acetone was added 7.65 g (0.013 mol) of bis(triphenylphosphine)tetrahydroboratocopper in one portion. After an hour the solution was filtered and the filtrate was evaporated to dryness. The residue was dissolved in 20 ml of chloroform and treated with 6 g of cuprous chloride, allowed to stir for an hour and filtered. The solvent was evaporated to dryness to yield 1.66 g (79 percent) of solid.

Workup

  1. filtrationAfter an hour the solution was filtered
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in 20 ml of chloroform
  4. additiontreated with 6 g of cuprous chloride
  5. filtrationfiltered
  6. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-93263f872ff54764a27a5ccb03a20505
Source dataset
uspto-grants-2006_03
Patent number
US07012121B2

Reaction notes

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