Ozone → (4,6-Dichloropyrimidin-5-yl)acetaldehyde

HRID 82248Notes

Reaction equation

HRID 82248 reaction equation
[CH2:1]([C:4]1[C:5]([Cl:11])=[N:6][CH:7]=[N:8][C:9]=1[Cl:10])[CH:2]=C.[O:12]=[O+][O-]>ClCCl>[Cl:11][C:5]1[C:4]([CH2:1][CH:2]=[O:12])=[C:9]([Cl:10])[N:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 24823OzoneHCID 5192085-Allyl-4,6-dichloropyrimidine

Product 1

HCID 13989292(4,6-Dichloropyrimidin-5-yl)acetaldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-Allyl-4,6-dichloro-pyrimidine (Preparation 207, 30 g, 0.159 mole) in dry dichloromethane (400 mL) was bubbled ozone at −70° C. for 30 min. After excess ozone was purged by nitrogen gas, dimethyl sulfide (10 mL) was added at −5° C., and the reaction was stirred for 2 hours. The mixture was washed with water, brine, dried over sodium sulfate, and evaporated in vacuo. The crude material was purified by trituration from pentane-diethyl ether to afford the title compound as a colorless solid in 84% yield, 10 g.

Workup

  1. customAfter excess ozone was purged by nitrogen gas, dimethyl sulfide (10 mL)
  2. additionwas added at −5° C.
  3. washThe mixture was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe crude material was purified by trituration from pentane-diethyl ether

Sources & evidence

ORD record
ord-d03ba48610ba49799669763cbcc35fad
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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