1-Iodonaphthalene → Naphthalene

HRID 984514Notes

Reaction equation

HRID 984514 reaction equation
CCCCCC.I[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH:16]1[C:17]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 70041-IodonaphthaleneHCID 8058Hexane

Product 1

HCID 931NaphthaleneYield 30%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Following General Procedure I, a mixture of hexane washed KH (160 mg, 4.0 mmol, 2.0 equiv), (Z)-21 (344 mg, 2.0 mmol, 1.0 equiv), 1-iodonaphthalene (292 μL, 2.0 mmol) and Pd(dba)2 (58 mg, 0.1 mmol, 0.05 equiv) was stirred in DME (4 mL) at room temperature for 15 min, and then was filtered through SiO2. Purification by column chromatography (RP C18, MeOH/H2O, 9/1) afforded 219 mg (49%) of (Z)-152a and 77 mg (30%) of naphthalene.

Workup

  1. filtrationwas filtered through SiO2
  2. customPurification by column chromatography (RP C18, MeOH/H2O, 9/1)

Sources & evidence

ORD record
ord-604c957b1eca40e79807a170af418ecb
Source dataset
uspto-grants-2005_03
Patent number
US06867323B2

Reaction notes

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