Pyridine → Methyl 2-cyano-4-(2-oxoethyl)benzoate

HRID 2173226Notes

Reaction equation

HRID 2173226 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]([CH2:13][CH:14]=C)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:2].N1C=CC=CC=1.[O:22]=[O+][O-].S(C)C>C(Cl)Cl.CO>[C:1]([C:3]1[CH:12]=[C:11]([CH2:13][CH:14]=[O:22])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1068Dimethyl SulfideHCID 24823OzoneHCID 67515990Methyl 2-cyano-4-(prop-2-en-1-yl)benzoate

Product 1

HCID 77230667Methyl 2-cyano-4-(2-oxoethyl)benzoate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
-78 °C

Procedure

The methyl 2-cyano-4-(prop-2-en-1-yl)benzoate (100 mg, 0.5 mmol) was dissolved in 1:1 CH2Cl2/MeOH (20 mL) containing pyridine (0.25%). The solution was cooled to −78° C., and O3 was passed through until a blue color was present. N2 was then bubbled through to discharge the blue color and Me2S (3 mol) was added. The reaction mixture was allowed to warm and left overnight. The mixture was washed with 1 N HCl and aqueous NaHCO3 and then dried and evaporated to give methyl 2-cyano-4-(2-oxoethyl)benzoate.

Workup

  1. customN2 was then bubbled through
  2. additionwas added
  3. temperatureto warm
  4. washThe mixture was washed with 1 N HCl and aqueous NaHCO3
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-5b7343ec730140d499dbfd767e008b90
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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