Dimethyl Sulfide → 2-(4-Iodophenyl)-2-methyloxirane

HRID 904233노트

반응식

HRID 904233 반응식
CSC.S([O:9][CH3:10])(OC)(=O)=O.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)=O.C[O-].[Na+]>C(#N)C>[I:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2([CH3:11])[CH2:10][O:9]2)=[CH:15][CH:16]=1

참가 물질

6

반응물 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 728691-(4-Iodophenyl)ethan-1-oneHCID 10942334Sodium Methoxide

생성물 1

HCID 233338282-(4-Iodophenyl)-2-methyloxirane수율 99.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

반응 조건

온도
25 °C

실험 절차

To a solution of 30 g of dimethyl sulfide in 30 ml of acetonitrile was added dropwise over a period of 30 minutes 30 g of dimethyl sulfate, while maintaining the temperature at 40° to 50° C., and the mixture was stirred for one hour at the same temperature. The reaction mixture was cooled to 25° C. and mixed with 30 g of 4-iodoacetophenone and 90 ml of acetonitrile. While stirring, 13.2 g of sodium methoxide was added to the mixture and stirring was continued for a further 30 minutes at room temperature to complete the reaction. Thereafter, the dimethyl sulfide and acetonitrile were removed by distillation, and to the residue were added 120 ml of cyclohexane and 120 ml of water, after which the mixture was thoroughly shaken. The organic layer was separated, dried over anhydrous magnesium sulfate, and freed from the solvent by distillation under reduced pressure to obtain 31.5 g (99% yield) of oily 2-(4-iodophenyl)-2-methyloxirane having a melting point of 44°-45° C.

후처리

  1. temperaturewhile maintaining the temperature at 40° to 50° C.
  2. stirringWhile stirring
  3. stirringstirring
  4. waitwas continued for a further 30 minutes at room temperature
  5. customthe reaction
  6. customThereafter, the dimethyl sulfide and acetonitrile were removed by distillation
  7. additionto the residue were added 120 ml of cyclohexane and 120 ml of water
  8. stirringafter which the mixture was thoroughly shaken
  9. customThe organic layer was separated
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationfreed from the solvent by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-975c4c8ded5a4cf8b32ea5624bac350c
출처 데이터셋
uspto-grants-1980_10
특허 번호
US04230719

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