HCID 12647522, compound → HCID 11195816, compound

HRID 2098981Notes

Reaction equation

HRID 2098981 reaction equation
[CH3:1][Mg]Br.[CH3:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][CH2:12][C:13]2=[C:16]([C:19]#[N:20])[C:17]#[N:18])=[CH:8][CH:7]=1>C1COCC1.[Cu]I>[CH3:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][CH2:12][C:13]2([CH:16]([C:19]#[N:20])[C:17]#[N:18])[CH3:1])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 12647522HCID 12647522, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 11195816HCID 11195816, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methylmagnesium bromide (3.0 M in diethyl ether (12.0 mL, 36.0 mmol)) and copper(I) iodide (6.86 g, 36.0 mmol) in THF (100 mL) was added 48.1 (6.73 g, 30.0 mmol) at room temperature. The resulting mixture was refluxed for 4 hours. The mixture was then cooled in an ice-bath, quenched with aqueous NH4Cl (200 mL), extracted with ether, concentrated, and purified by silica gel column chromatography to give 48.2 (4.8 g, 66% yield). MS ESI (pos.) M/E: 241 (M+H).

Workup

  1. temperatureThe resulting mixture was refluxed for 4 hours
  2. temperatureThe mixture was then cooled in an ice-bath
  3. customquenched with aqueous NH4Cl (200 mL)
  4. extractionextracted with ether
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e3b5e43dea144517944eee22c2a24923
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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