Tetrahydrofuran → 1-(4-(Methylthio)phenyl)ethan-1-one

HRID 2298119Notes

Reaction equation

HRID 2298119 reaction equation
[CH3:1][S:2][C:3]1C=CC(C#N)=[CH:5][CH:4]=1.[CH3:11][Li].[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>>[CH3:11][C:15]([C:14]1[CH:13]=[CH:17][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1)=[O:16]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 5909604-(Methylthio)benzonitrileHCID 178418348HCID 178418348, compound

Product 1

HCID 745011-(4-(Methylthio)phenyl)ethan-1-one

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4-(methylthio)benzonitrile (50 g, 340 mmol) in THF (2 L) at −78° C., was added methyllithium (282 ml, 1.4 M in diethyl ether, 390 mmol) over a period of ten minutes. The solution was stirred at −78° C. for one hour and then the dry ice bath was removed. After five hours, 100 ml of water followed by 200 ml of 3N HCl were added to the reaction mixture and it was stirred overnight. Concentration in vacuo gave a residue which was partitioned between ethyl acetate and water. The water layer was extracted with three portions of ethyl acetate and the combined ethyl acetate layers were dried (MgSO4). Concentration in vacuo gave 58 g of crude 4-(methylthio)acetophenone as a yellow solid: 1H NMR (CDCl3) δ 2.52 (s, 3H), 2.57 (s, 3H), 7.26 (d, J=8.7 Hz, 2H), 7.87 (d, J=8.7 Hz, 2H). The sample was used without further purification.

Workup

  1. customthe dry ice bath was removed
  2. waitAfter five hours
  3. additionwere added to the reaction mixture and it
  4. stirringwas stirred overnight
  5. concentrationConcentration in vacuo
  6. customgave a residue which
  7. customwas partitioned between ethyl acetate and water
  8. extractionThe water layer was extracted with three portions of ethyl acetate
  9. dry with materialthe combined ethyl acetate layers were dried (MgSO4)
  10. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-e5357ee177344aa6a43be01309b795c9
Source dataset
uspto-grants-2002_12
Patent number
US06492413B2

Reaction notes

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