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(1-Chloroethyl)benzene → 2-methoxy-5-[(E,3S)-3-phenylbut-1-enyl]pyrimidine

HRID 1422369
Notes
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Reaction equation

HRID 1422369 reaction equation
CC(Cl)c1ccccc1.COc1ncc(/C=C/Br)cn1>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>COc1ncc(/C=C/[C@H](C)c2ccccc2)cn1
ParticipantsConditionsWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 12648(1-Chloroethyl)benzeneHCID 178494162HCID 178494162, compound

Product 1

HCID 1624022622-methoxy-5-[(E,3S)-3-phenylbut-1-enyl]pyrimidineYield 57%

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-f329a2f4290c42fa85d2c5a14e0d4667
Source dataset
Electroreductive Coupling of Alkenyl and Benzyl Halides
DOI
10.1021/acscatal.9b01785
Original link
View source

Reaction notes

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On this pageParticipantsConditionsWorkupSources & evidenceReaction notes