2-Bromobutane → 2-(sec-butoxy)-1H-isoindole-1,3(2H)-dione

HRID 29158

반응식

HRID 29158 반응식
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].N12CCCN=C1C[CH2:17][CH2:16][CH2:15][CH2:14]2.BrC(CC)C>CN(C=O)C>[CH:15]([O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7])([CH2:16][CH3:17])[CH3:14]

참가 물질

5

반응물 3

HCID 65542-BromobutaneHCID 10665N-HydroxyphthalimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

생성물 1

HCID 108227352-(sec-butoxy)-1H-isoindole-1,3(2H)-dione수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

N-hydroxylphthalimide (18.4 mmol, 3.0 g) was dissolved in anhydrous DMF (20 mL) under nitrogen. To the stirring solution, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (27.6 mmol, 4.13 mL) was injected followed by 2-bromobutane (22.1 mmol, 2.41 mL) and the reaction was warmed to 55° C. After stirring for 18 hour, the reaction was cooled to room temperature and concentrated to a red oil. The reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with saturated aqueous sodium bicarbonate solution, distilled water, brine and dried over magnesium sulfate. The solvent was removed under vacuum providing 3.57 g (89%) of a yellow solid. Rf: 0.8 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73 (2H,m), 4.31 (1H,m), 1.81 (1H,m), 1.64 (1H,m), 1.32 (3H,d), 1.03 (3H,t).

후처리

  1. temperaturethe reaction was cooled to room temperature
  2. concentrationconcentrated to a red oil
  3. customThe reaction was partitioned between ethyl acetate and 1N HCl
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  5. distillationdistilled water, brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-dfeb3f265d5d446e915bd4f1737a0a9c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419967B2

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