Ethyl 4-iodobenzoate → HCID 59925992, compound

HRID 984520Notes

Reaction equation

HRID 984520 reaction equation
O([Si](C)(C)C)[K].[CH2:7]([O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)[CH3:8]>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]>[CH2:7]([O:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14](/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:13][CH:12]=1)[CH3:8]

Participants

4

Reactant 2

HCID 142891Ethyl 4-iodobenzoateHCID 178504318HCID 178504318, compound

Product 1

HCID 59925992HCID 59925992, compound

Reagents, catalysts & solvents 1

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst

Procedure

Following General Procedure II, a mixture of KOSiMe3 (570 mg, 4.0 mmol, 2.0 equiv), (Z)-21 (379 mg, 2.2 mmol, 1.1 equiv), ethyl-4-iodobenzoate (2.0 mmol) and Pd(dba)2 (58 mg, 0.1 mmol, 0.05 equiv) was stirred at room temperature for 15 min, and then was filtered through SiO2. Purification by column chromatography (RP C18, MeOH/H2O, 9/1) and Kugelrohr distillation afforded 411 mg (83%) of (Z)-154f as colorless oil.

Workup

  1. filtrationwas filtered through SiO2
  2. customPurification
  3. distillationby column chromatography (RP C18, MeOH/H2O, 9/1) and Kugelrohr distillation
  4. customafforded 411 mg (83%) of (Z)-154f as colorless oil

Sources & evidence

ORD record
ord-9aa24632910e4d07903f7f465a51eaf0
Source dataset
uspto-grants-2005_03
Patent number
US06867323B2

Reaction notes

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