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Dimethylformamide → 2-(4-Methoxy-2,3-dimethylphenyl)-1-(pyrrolidin-1-yl)ethanone

HRID 2423285
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HRID 2423285 반응식
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH3:12])[C:5]=1[CH3:13].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.CN(C=[O:24])C>O.CCOCC>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][C:2]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:24])=[C:5]([CH3:13])[C:6]=1[CH3:12]
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참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 59864791HCID 59864791, 화합물

생성물 1

HCID 598648482-(4-Methoxy-2,3-dimethylphenyl)-1-(pyrrolidin-1-yl)ethanone

시약·촉매·용매 2

HCID 962Water용매2회HCID 3283Diethyl Ether용매

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온도
80 °C

실험 절차

Under an N2 atmosphere, 1-(2,2-dibromovinyl)-4-methoxy-2,3-dimethylbenzene was dissolved in a mixture of DMF (43 mL) and water (14 mL). Pyrrolidine (5.67 mL, 68 mmol) was added and the reaction was heated to 80° C. for 20 h. The reaction was diluted with Et2O and water. The layers were separated and the organic layer was washed with 0.25M HCl (aq) and brine. The organic extract was dried (Na2SO4), filtered, and concentrated in vacuo. Flash column chromatography of the residue, eluting with 0% to 100% ethyl acetate in hexanes, afforded the title compound. LC-MS ESI (pos.) m/z: 248.2 (M+H).

후처리

  1. customThe layers were separated
  2. washthe organic layer was washed with 0.25M HCl (aq) and brine
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washFlash column chromatography of the residue, eluting with 0% to 100% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-ff444e80e37843a2800e226d1dabe5dd
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960567B2

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