3,4-dihydro-2H-pyran → 2-(Oxan-2-yloxy)isoindole-1,3-dione

HRID 874519노트

반응식

HRID 874519 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].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>C(Cl)Cl.O1CCOCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[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]

참가 물질

6

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 10665N-Hydroxyphthalimide

생성물 1

HCID 2895872-(Oxan-2-yloxy)isoindole-1,3-dione수율 88.3%

시약·촉매·용매 3

HCID 6101p-Toluenesulfonic acid촉매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

to a vigorously stirred solution of N-hydroxyphthalimide (10.0 g, 61.4 mmol) in CH2Cl2 (70 mL) and dioxane (80 mL) was added dihydropyran (6.16 mL, 67.6 mmol) and p-toluenesulfonic acid (200 mg). The resulting solution was stirred overnight at room temperature. The reaction was quenched by slow addition of saturated NaHCO3 (100 mL). After separation, the organic layer was washed with brine and dried over Na2SO4. Solvent removal under vacuum yielded 13.4 g (88%) of 2-(tetrahydro-2H-pyran-2-yloxy)isoindoline-1,3-dione as a white solid.

후처리

  1. customThe reaction was quenched by slow addition of saturated NaHCO3 (100 mL)
  2. customAfter separation
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customSolvent removal under vacuum

출처 및 근거

ORD 기록
ord-13cb4623d1bd43ea94c508923fd50c3a
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980909B2

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