Sodium hydride → HCID 57441044, compound

HRID 1663663Notes

Reaction equation

HRID 1663663 reaction equation
[C:1]([CH:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:4])#[N:2].C[O-].[Na+].Br[CH2:19][CH:20]1[CH2:22][CH2:21]1.[H-].[Na+]>C(#N)C.C(OCC)C>[C:1]([C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])[CH2:19][CH:20]1[CH2:22][CH2:21]1)#[N:2]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 10035402Methyl 3-(1-cyanoethyl)benzoateHCID 10942334Sodium Methoxide

Product 1

HCID 57441044HCID 57441044, compoundYield 6.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 3-(1-cyanoethyl)benzoate (1.5 g, 7.9=mol) in acetonitrile (20 mL) were added sodium methoxide (0.95 g, 17 mmol) and (bromomethyl)cyclopropane (1.3 g, 9.5 mmol), and the reaction mixture was stirred at room temperature for 30 min. To the reaction mixture was added sodium hydride (60% in oil, 0.7 g, 17 mmol) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. The mixture was diluted with diethyl ether, and washed with 5% aqueous sodium hydrogencarbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→40/60) to give the title compound (129 mg, 6.7%) as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 16 hr
  3. washwashed with 5% aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltrated
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→40/60)

Sources & evidence

ORD record
ord-996f746b6fbc4cb39d4f3cc517c83cc6
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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