Hydrochloric Acid → 1-(2-Chloropyrimidin-5-yl)ethan-1-one

HRID 1046097Notes

Reaction equation

HRID 1046097 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10]CC)=[CH2:9])=[CH:4][N:3]=1.Cl>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 143210022-Chloro-5-(1-ethoxyvinyl)pyrimidine

Product 1

HCID 137157421-(2-Chloropyrimidin-5-yl)ethan-1-oneYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-5-(1-ethoxyvinyl)pyrimidine (350 mg, 1.9 mmol) in THF (15 mL) was, added aqueous HCl (1N, 15 mL). The mixture was stirred at rt for 4 h, extracted with EtOAc. The organic phase was washed with satd aq NaHCO3 and brine. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give the crude product, which was purified by prep TLC (PE:EA 3:1) to give 1-(2-chloropyrimidin-5-yl)ethanone (268 mg, yield 90%).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with satd aq NaHCO3 and brine
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by prep TLC (PE:EA 3:1)

Sources & evidence

ORD record
ord-b0a1778b1c8147f29f11d304aa62e664
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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