Pyridine → HCID 86694487, compound

HRID 1519643Notes

Reaction equation

HRID 1519643 reaction equation
[CH2:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([O:12][CH:13]2[CH2:15][CH2:14]2)[CH:5]=1)[CH:2]=C.N1C=CC=CC=1.[O:22]=[O+][O-]>C(Cl)Cl.CO>[CH:13]1([O:12][C:6]2[CH:5]=[C:4]([CH2:1][CH:2]=[O:22])[CH:11]=[CH:10][C:7]=2[C:8]#[N:9])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24823OzoneHCID 67513375HCID 67513375, compound

Product 1

HCID 86694487HCID 86694487, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 4-allyl-2-(cyclopropyloxy)benzonitrile (100 mg, 0.5 mmol) in 1:1 CH2Cl2/MeOH (15 mL) containing pyridine (0.5 mL, 6 mmol) 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 (5 ml) 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 concentrated to give crude 2-(cyclopropyloxy)-4-(2-oxoethyl)benzonitrile.

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. concentrationconcentrated

Sources & evidence

ORD record
ord-5d165feb6ffa492590a3695e6b905555
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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