(1-Chloroethyl)benzene → (E,5S)-5-phenylhex-3-en-1-ol

HRID 1422372Notes

Reaction equation

HRID 1422372 reaction equation
CC(Cl)c1ccccc1.OCC/C=C/Br>CC(=O)N(C)C.COCCOC.[Cl][Ni][Cl].[I-].[Na+].c1ccc2c(c1)C[C@@H]1OC(C3(C4=N[C@@H]5c6ccccc6C[C@@H]5O4)CC3)=N[C@H]21>C[C@@H](/C=C/CCO)c1ccccc1

Participants

7

Reactant 2

HCID 12648(1-Chloroethyl)benzeneHCID 14740944(3E)-4-bromobut-3-en-1-ol

Product 1

HCID 162402402(E,5S)-5-phenylhex-3-en-1-olYield 56%

Reagents, catalysts & solvents 4

HCID 5238Sodium IodideReagentHCID 11245230(3aR,3a'R,8aS,8a'S)-2,2'-(Cyclopropane-1,1-diyl)bis(8,8a-dihydro-3aH-indeno[1,2-d]oxazole)CatalystHCID 15773433Dichloronickel;1,2-dimethoxyethaneCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Workup

  1. additionNo procedure recorded
  2. additionNo procedure recorded
  3. extractionKeep organic
  4. additionNo procedure recorded
  5. extractionKeep organic
  6. additionNo procedure recorded
  7. extractionKeep organic
  8. washNo procedure recorded
  9. dry with materialNo procedure recorded
  10. filtrationKeep filtrate
  11. concentrationNo procedure recorded

Sources & evidence

ORD record
ord-a1674a7659ec4286a3ba520bab2e5c74
Source dataset
Electroreductive Coupling of Alkenyl and Benzyl Halides
Original link
View source

Reaction notes

Loading…