Trimethylsulfonium iodide → HCID 59454960, compound

HRID 1401569Notes

Reaction equation

HRID 1401569 reaction equation
[CH3:1]C(C)([O-])C.[K+].[I-].C[S+](C)C.[CH3:12][CH:13]([CH3:22])[C:14]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[O:15]>O>[CH:13]([C:14]1([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:1][O:15]1)([CH3:22])[CH3:12]

Participants

5

Reactant 3

HCID 75127Trimethylsulfonium iodideHCID 10898858HCID 10898858, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 59454960HCID 59454960, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Potassium tert-butoxide (0.098 g, 0.80 mmol) and trimethylsulfonium iodide (0.164 g, 0.8 mmol) were mixed at RT and stirred at 0° C. To this was added 2-methyl-1-(pyridin-4-yl)propan-1-one (0.100 g, 0.671 mmol) slowly. The reaction mixture was stirred at 0° C. for 15 min. and then warmed to and stirred at 70° C. for 1 h. The reaction mixture diluted with water and extracted with EtOAc (3 10 mL), organic layer dried on sodium sulfate and concentrated under vacuum to obtain 4-(2-isopropyloxiran-2-yl)pyridine (0.1 g). 1H NMR (CDCl3, freebase) δ (ppm): 8.6 (d, 2H), 7.26 (d, 2H), 3.05 (d, 1H), 2.29 (septet, 1H), 2.26 (d, 1H), 1.65 (d, 6H).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 15 min.
  2. temperaturewarmed to and
  3. stirringstirred at 70° C. for 1 h
  4. extractionextracted with EtOAc (3 10 mL), organic layer
  5. customdried on sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-96c5827e4e18412fb3a5b0cd8e03c372
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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