Ethyl Acetate → 1-(3,4,5-Trimethoxybenzyl)-2-oxopyrrolidine

HRID 323259

반응식

HRID 323259 반응식
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].C[Si]([N-][Si](C)(C)C)(C)C.[K+].S(O[CH2:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=1)(=O)(=O)C.C(OCC)(=O)C>O1CCCC1>[CH3:34][O:33][C:25]1[CH:24]=[C:23]([CH:28]=[C:27]([O:29][CH3:30])[C:26]=1[O:31][CH3:32])[CH2:22][N:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 120252-PyrrolidoneHCID 3251421Potassium bis(trimethylsilyl)amideHCID 184645913,4,5-Trimethoxybenzyl Mesylate2회

생성물 1

HCID 184646621-(3,4,5-Trimethoxybenzyl)-2-oxopyrrolidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

Combine 2-pyrrolidinone (2.85 g, 33.5 mmol) and tetrahydrofuran (70 mL). Cool to −78° C. using a dry-ice/acetone bath. Add a solution of potassium bis(trimethylsilyl)amide (67 mL, 0.5 M in toluene, 33.5 mol). After 45 minutes, add a solution of 3,4,5-trimethoxybenzyl mesylate (8.8 g, 32.02 mmol) in tetrahydrofuran (60 mL). After the addition of 3,4,5-trimethoxybenzyl mesylate is complete, heat to reflux. After 18 hours, cool the reaction mixture and partition between water and ethyl acetate. Separate the aqueous layer and extract 4 times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound: Rf=0.35 (silica gel, ethyl acetate).

후처리

  1. temperatureheat to reflux
  2. waitAfter 18 hours
  3. temperaturecool the reaction mixture
  4. custompartition between water and ethyl acetate
  5. customSeparate the aqueous layer
  6. extractionextract 4 times with ethyl acetate
  7. dry with materialDry the combined organic layers over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customto obtain a residue

출처 및 근거

ORD 기록
ord-a3c903c1840e48eaab629b6bd9865ccc
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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