Tetrahydrofuran → HCID 13765240, compound

HRID 1665441Notes

Reaction equation

HRID 1665441 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5]C=1.Cl[CH2:12]C(C)=C.[Cl-].[NH4+].S([O-])([O-])(=O)=O.[Na+].[Na+].O1[CH2:29][CH2:28][CH2:27][CH2:26]1>[Cu](I)I.[I-]>[CH2:27]([C:28]1[CH:29]=[CH:5][C:6]([CH2:7][C:8]([CH3:3])=[CH2:12])=[CH:9][CH:10]=1)[CH3:26]

Participants

9

Reactant 6

HCID 8028Tetrahydrofuran2×HCID 112413-Chloro-2-methyl-1-propeneHCID 153131-Bromo-4-ethylbenzeneHCID 24436Sodium SulfateHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 13765240HCID 13765240, compound

Reagents, catalysts & solvents 2

HCID 30165Iodide IonCatalystHCID 83717Copper iodideCatalyst

Procedure

Under nitrogen atmosphere, tetrahydrofuran (KANTO, 8.1 mL) was added to magnesium (WAKO, 263 mg) and iodide (WAKO, 1 mg), followed with addition of tetrahydrofuran (KANTO, 5.5 mL) solution comprising 1-bromo-4-ethylbenzene (TCI, 2.0 g). The mixture was stirred at room temperature for 30 minutes. The reaction solution was cooled to 0° C. and added with copper iodide (WAKO, 205 mg) and 3-chloro-2-methyl-1-propene (WAKO, 1.32 mL) followed by stirring at room temperature for 1 hour and 30 minutes. The reaction solution was cooled and added with saturated ammonium chloride solution, and further added with sodium sulfate. The reaction mixture was filtered, and concentrated under reduced pressure to obtain a crude product, which was then purified by silica gel column chromatography to obtain the target compound (500 mg).

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. stirringby stirring at room temperature for 1 hour and 30 minutes
  3. temperatureThe reaction solution was cooled
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a crude product, which
  7. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-68679f2e96e84f699064be164b03f55a
Source dataset
uspto-grants-2011_10
Patent number
US08039514B2

Reaction notes

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