Diethyl Ether → 2-Cyclobutanecarbonylpyridine

HRID 900758Notes

Reaction equation

HRID 900758 reaction equation
[CH:1]1([Mg]Br)[CH2:4][CH2:3][CH2:2]1.[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)#N.CC[O:17]CC>>[CH:1]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:17])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 7522Pyridine-2-carbonitrileHCID 178419648HCID 178419648, compound

Product 1

HCID 247235492-CyclobutanecarbonylpyridineYield 83%

Procedure

To an etheral solution of cyclobutyl magnesium bromide (prepared from bromocyclobutane (970 mg, 7.18 mmol) and magnesium (175 mg, 7.18 mmol) in ether (20 ml)) was dropwise added a solution of 2-cyanopyridine (748 mg, 7.18 mmol) in ether (10 ml) at room temperature. After 2 hours, the reaction was quenched by addition of an aqueous saturated solution of NH4Cl. The mixture was extracted with ether. The organic phase was dried over MgSO4 and concentrated under vacuum. The residue was purified by chromatography on silica gel (hexane/AcOEt 95/5) to give the cyclobutyl(2-pyridinyl)methanone 7 as colorless oil (960 mg, 83%).

Workup

  1. customthe reaction was quenched by addition of an aqueous saturated solution of NH4Cl
  2. extractionThe mixture was extracted with ether
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by chromatography on silica gel (hexane/AcOEt 95/5)

Sources & evidence

ORD record
ord-711f7bdcc41d46af90418bca0e9ffc6c
Source dataset
uspto-grants-2008_04
Patent number
US07361668B2

Reaction notes

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