4-Cyanobenzaldehyde → HCID 10583039, compound

HRID 844004Notes

Reaction equation

HRID 844004 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:2].[C:11]([Mg]Br)#[CH:12]>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)[C:11]#[CH:12]

Participants

4

Reactant 2

HCID 660424-CyanobenzaldehydeHCID 178418486HCID 178418486, compound

Product 1

HCID 10583039HCID 10583039, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-Formyl-benzonitrile (1.5 grams, 10.0 mmole) in tetrahydrofuran (20 ml) at −78° C. was added 0.5 M ethynyl magnesium bromide (26 ml, 13.0 mmole) dropwise. The mixture was stirred at −78° C. for 30 minutes and allowed to warm to room temperature over one hour. The reaction was cooled to 0° C., quenched with 10 ml methanol, poured into 200 ml water, acidified with oxalic acid and extracted with diethyl ether. The combined extracts were washed with water and brine, dried over MgSO4, filtered, and concentrated to give an oil which was purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent to give a solid. (1.6 g). MW 157.18; MS (m/e) 157 (M+).

Workup

  1. temperatureto warm to room temperature over one hour
  2. temperatureThe reaction was cooled to 0° C.
  3. customquenched with 10 ml methanol
  4. additionpoured into 200 ml water
  5. extractionextracted with diethyl ether
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an oil which
  11. customwas purified via flash chromatography on silica using 30% ethyl acetate/hexane as eluent
  12. customto give a solid

Sources & evidence

ORD record
ord-9cfc79f694de45bd813e09e85ebce7f5
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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