1-Iodonaphthalene → HCID 11379100, compound

HRID 984515Notes

Reaction equation

HRID 984515 reaction equation
O([Si](C)(C)C)[K].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>>[CH:17](/[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 70041-IodonaphthaleneHCID 178504318HCID 178504318, compound

Product 1

HCID 11379100HCID 11379100, compound

Procedure

Following General Procedure II, a mixture of KOSiMe3 (570 mg, 4.0 mmol, 2.0 equiv), (E)-21 (379 mg, 2.2 mmol, 1.1 equiv), 1-iodonaphthalene (292 μL, 2.0 mmol) and Pd(dba) (58 mg, 0.1 mmol, 0.05 equiv) was stirred at room temperature for 2 h, and then was filtered through SiO2. Purification by column chromatography (RP C18, MeOH/H2O, 9/1) and Kugelrohr distillation afforded 416 mg (93%) of (E)-154a 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 416 mg (93%) of (E)-154a as colorless oil

Sources & evidence

ORD record
ord-bb14930002e04f358d5e38e565935651
Source dataset
uspto-grants-2005_03
Patent number
US06867323B2

Reaction notes

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