Water → 3-Chloro-1-phenylpyrrolidin-2-one

HRID 271232노트

반응식

HRID 271232 반응식
[C:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.S([Cl:33])(C1C=CC(C)=CC=1)(=O)=O.O>C1COCC1.CCOC(C)=O>[Cl:33][CH:9]1[CH2:10][CH2:11][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]1=[O:12]

참가 물질

7

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 783751-Phenylpyrrolidin-2-oneHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 219355593-Chloro-1-phenylpyrrolidin-2-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

1-Phenyl-2-pyrrolidinone (1 g, 6.2 mmol) in THF (60 mL, anhydrous) was cooled to −40° C. and LiHMDS (8 mL, 8 mmol, 1 M soln. in THF) was added. The resulting solution was stirred for 40 min. and tosyl chloride (1.78 g, 9.33 mmol) was then added. After warming the solution to RT over a 14 hour period, H2O added to quench reaction. The solution was then concentrated to provide an oil. Next, the oil was redissovled in EtOAc and washed with H2O and brine. The organic layer was dried over Na2SO4, filtered, and concentrated to an oil once again. Purified via flash column chromatography (4:1 hexane/EtOAc) provided 3-chloro-1-phenylpyrrolidin-2-one.

후처리

  1. additionadded
  2. customto quench
  3. customreaction
  4. concentrationThe solution was then concentrated
  5. customto provide an oil
  6. washwashed with H2O and brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to an oil once again
  10. customPurified via flash column chromatography (4:1 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-1690da9ee9d04d15a9e902f5e916c3ee
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452889B2

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