1,10-Phenanthroline → HCID 15352592, compound

HRID 1883425Notes

Reaction equation

HRID 1883425 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].I[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.[CH3:30][CH:31]([OH:34])[CH:32]=[CH2:33]>[Cu]I.C1(C)C=CC=CC=1>[CH3:30][CH:31]([O:34][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH:32]=[CH2:33]

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 117163-Buten-2-olHCID 696764-Iodoanisole

Product 1

HCID 15352592HCID 15352592, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A test tube was charged with CuI (20 mg, 0.10 mmol, 0.10 equiv), 1,10-phenanthroline (36 mg, 0.20 mmol, 0.20 equiv), Cs2CO3 (652 mg, 2.0 mmol, 2.0 equiv), 4-iodoanisole (234 mg, 1.0 mmol, 1.0 equiv), 3-buten-2-ol (180 μL, 2.0 mmol, 2.0 equiv) and toluene (0.5 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 38 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (2×20 cm; pentane:diethyl ether 30:1) provided 96 mg (54% yield) of the known title compound as a colorless oil.

Workup

  1. customThe test tube was sealed
  2. temperatureThe resulting suspension was cooled to room temperature
  3. filtrationfiltered through a 0.5×1 cm pad of silica gel
  4. washeluting with diethyl ether
  5. concentrationThe filtrate was concentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (2×20 cm; pentane:diethyl ether 30:1)

Sources & evidence

ORD record
ord-0699b9e073214623a5dd4e5c8b072d79
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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