Methyl iodide → HCID 63346625, compound

HRID 1855392Notes

Reaction equation

HRID 1855392 reaction equation
CI.[CH3:3][C:4]1[N:8]=[C:7]([CH2:9][C:10](=[O:12])[CH3:11])[O:6][N:5]=1.[C:13](=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CCCCCCC>[CH3:3][C:4]1[N:8]=[C:7]([CH:9]([CH3:13])[C:10](=[O:12])[CH3:11])[O:6][N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 129553831-(3-Methyl-1,2,4-oxadiazol-5-yl)propan-2-one

Product 1

HCID 63346625HCID 63346625, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
20 °C

Procedure

Methyl iodide (0.375 ml, 6 mmol) was added to a mixture of 1-(3-methyl-[1,2,4]oxadiazol-5-yl)-propan-2-one (0.84 g, 6 mmol) and potassium carbonate (4.15 g, 30 mmol) in acetoniotrile (8 mL), and the mixture was stirred at 20° C. for 12 h. Insoluble material was filtered off and the filtrate was diluted with dichloromethane. The solution was washed with 1 N hydrochloric acid and with brine, dried over sodium sulfate, and evaporated under reduced pressure. The residual oil was subjected to column chromatography on silica gel. Heptane/0-20% ethyl acetate eluted successively the title compound 3-methyl-3-(3-methyl-[1,2,4]oxadiazol-5-yl)-butan-2-one (181 mg, 18%), obtained as colorless oil, Rf 0.4 (SiO2, ethyl acetate/heptane 1:1), MS ISP (m/e): 169.1 [(M+H)+]; 3-(3-Methyl-[1,2,4]oxadiazol-5-yl)-butan-2-one (296 mg, 3 2%), obtained as colorless oil, Rf 0.2 (SiO2, ethyl acetate/heptane 1:1), MS ISP (m/e): 155.1 [(M+H)+]; and 3-hydroxy-3-(3-methyl-[1,2,4]oxadiazol-5-yl)-butan-2-one (204 mg, 20%), obtained as colorless oil, Rf 0.1 (SiO2, ethyl acetate/heptane 1:1),

Workup

  1. filtrationInsoluble material was filtered off
  2. additionthe filtrate was diluted with dichloromethane
  3. washThe solution was washed with 1 N hydrochloric acid and with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. washHeptane/0-20% ethyl acetate eluted successively the title compound 3-methyl-3-(3-methyl-[1,2,4]oxadiazol-5-yl)-butan-2-one (181 mg, 18%)
  7. customobtained as colorless oil, Rf 0.4 (SiO2, ethyl acetate/heptane 1:1), MS ISP (m/e)

Sources & evidence

ORD record
ord-cdabf9cc7b4640f38874031b0d580d85
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

Loading…