Diethyl Ether → HCID 86648062, compound

HRID 2098972Notes

Reaction equation

HRID 2098972 reaction equation
[F:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[C:11]([C:14]#[N:15])[C:12]#[N:13])[CH2:8][CH2:7]2.[CH3:18][Mg]Br.C(OCC)C>C1COCC1.[Cu]I>[F:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9]([CH:11]([C:12]#[N:13])[C:14]#[N:15])([CH3:18])[CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 86648061HCID 86648061, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 86648062HCID 86648062, compoundYield 68%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 38.2 (260 mg, 1.1 mmol) in THF (7.0 mL) was added copper(I) iodide (260 mg, 1.4 mmol) followed by a 3.0M solution of methylmagnesium bromide in diethyl ether (0.45 mL, 1.4 mmol). The mixture was heated to reflux and stirred for one hour. The reaction was then cooled to room temperature and quenched with a saturated ammonium chloride solution. The mixture was extracted with EtOAc (2×) and the combined organic layers were dried over magnesium sulfate. The residue was purified by medium pressure chromatography (silica, 25 to 50% EtOAc:hexanes) to yield 38.3 (190 mg, 68% yield). MS ESI (neg.) m/e: 243.1 (M−H)−.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customquenched with a saturated ammonium chloride solution
  4. extractionThe mixture was extracted with EtOAc (2×)
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. customThe residue was purified by medium pressure chromatography (silica, 25 to 50% EtOAc:hexanes)

Sources & evidence

ORD record
ord-e364d607ac04498c881e51dafaf93eb3
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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