Pyridine → Phenyl vinyl sulfone

HRID 1075497

반응식

HRID 1075497 반응식
[C:1]1([S:7]([CH2:10][CH2:11]O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.S(Cl)(Cl)=O.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[C:1]1([S:7]([CH:10]=[CH2:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 302022-(Phenylsulfonyl)ethanolHCID 516892Sodium Bicarbonate

생성물 1

HCID 79664Phenyl vinyl sulfone수율 98%

시약·촉매·용매 1

HCID 1140Toluene용매3회

반응 조건

온도
60 °C

실험 절차

2-(phenylsulfonyl)ethanol (143.8 g, purity 96.2%, 743 mmol) was added to 71.9 g of toluene, and 30.0 g (38 mmol) of pyridine was added to the mixture. The resulting solution was heated to 60° C., then 110.5 g (929 mmol) of thionyl chloride added over 5 hours at 60 to 70° C., and the mixture was stirred for 2 hours at 70° C. Then, the mixture was diluted with 143.9 g of toluene and cooled to 45° C. Then 303.2 g of 7% sodium bicarbonate solution and 193.4 g of toluene were added, washed separated. Obtained organic layer was mixed with 303.2 g of 7% sodium bicarbonate solution and stirred and separated. 5 g of the organic layer was sampled and subjected to HPLC analysis, which revealed that (β-chloroethylsulfonyl)benzene was obtained in a yield of 98% and phenylvinylsulfone in a yield of 0.7%. (Internal Standard: methyl benzoate).

후처리

  1. additionwas added to the mixture
  2. temperaturecooled to 45° C
  3. washwashed
  4. customseparated
  5. additionObtained organic layer was mixed with 303.2 g of 7% sodium bicarbonate solution
  6. stirringstirred
  7. customseparated
  8. aliquot5 g of the organic layer was sampled

출처 및 근거

ORD 기록
ord-9456b4a8742c442b87542d0c5aa9de23
출처 데이터셋
uspto-grants-1999_05
특허 번호
US05902905

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