Hydrochloric Acid → 1-(4-Methyl-3-pyridinyl)ethanone

HRID 633718Notes

Reaction equation

HRID 633718 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].CC[CH2:11][CH2:12][O:13]C=C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>O.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:12](=[O:13])[CH3:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11430Potassium Carbonate2×HCID 812191,3-Bis(diphenylphosphino)propaneHCID 8176303-Bromo-4-methylpyridine

Product 1

HCID 109424811-(4-Methyl-3-pyridinyl)ethanoneYield 40.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

671 μl (5.81 mmol) of 3-bromo-4-methylpyridine in 15 mL of H2O/DMF (1/4: v/v), 1.93 mL (14.53 mmol) of N-butyl vinyl ether, 39.15 mg (0.17 mmol) of palladium(II) acetate, 163.14 mg (0.38 mmol) of 1,3-bis(diphenylphosphino)propane and 973.84 mg (6.98 mmol) of potassium carbonate are placed in a microwave tube. After irradiating with microwaves at 120° C. for 2 hours, 20 mL of 5% hydrochloric acid solution are added. The reaction mixture is stirred for 1 hour at room temperature and then basified with potassium carbonate and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane) to give 320 mg of 1-(4-methylpyrid-3-yl)ethanone, the characteristics of which are as follows:

Workup

  1. customAfter irradiating with microwaves at 120° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane)

Sources & evidence

ORD record
ord-410cfb11182c46be9c9963fb1bcc3b2f
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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