Water → 1-(4-Pyridinyl)-1-propanone

HRID 371398Notes

Reaction equation

HRID 371398 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)#N.[OH:13]S(O)(=O)=O.O>C(OCC)C>[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)(=[O:13])[CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 75064-CyanopyridineHCID 178418443HCID 178418443, compound

Product 1

HCID 743431-(4-Pyridinyl)-1-propanoneYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2.845M ethylmagnesium bromide (263 mL, 0.75 mol) in ethyl ether (Et2O) (250 mL) was slowly added a solution of 4-cyanopyridine (39 g, 0.375 mol) in Et2O (750 mL). The reaction mixture was warmed at reflux for 12 hours, treated with concentrated H2SO4 (125 mL)/H2O (125 mL), and then washed three times with Et2O (250 mL). The aqueous portion was made basic (pH 9) with 15% NaOH solution and extracted five times with 250 mL portions of Et2O. The combined Et2O extracts were dried (MgSO4), and the solvent was removed under reduced pressure to afford a brown oil (48.4 g, 95%). Purification by vacuum distillation at 93°-97° (2.6 mm) afforded product as a pale yellow oil (25.35 g, 50%), NMR (CDCl3) δ 1.23 (t, 3H, J= 7 Hz), 3.00 (q, 2H, J=7 Hz), 7.70 (d, 2H, J=6 Hz), and 8.78 (d, 2H, J=6 Hz); IR (film) 1695 cm-1.

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureat reflux for 12 hours
  3. washwashed three times with Et2O (250 mL)
  4. extractionextracted five times with 250 mL portions of Et2O
  5. dry with materialThe combined Et2O extracts were dried (MgSO4)
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-75742fbddcc145bb8984567f408c68ec
Source dataset
uspto-grants-1985_07
Patent number
US04532250

Reaction notes

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