Methanesulfonic Acid → Phthalimide

HRID 1050458

반응식

HRID 1050458 반응식
C(OC(=O)C)(=O)C.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.O=C(C)CC[N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41]>CCOC(C)=O>[C:32]1(=[O:41])[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:39](=[O:40])[NH:31]1

참가 물질

6

반응물 4

HCID 6395Methanesulfonic AcidHCID 7918Acetic AnhydrideHCID 14812Phosphorus oxide (P4O10)HCID 2907282-(3-Oxobutyl)isoindoline-1,3-dione

생성물 1

HCID 6809Phthalimide수율 22.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

To a stirred solution of acetic anhydride (5.0 mL, 53.0 mmol) and 7.7 wt % phosphorus pentoxide in methanesulfonic acid (Eaton's Reagent) (5.0 mL, 4.60 mmol) was added 2-(3-oxobutyl)isoindoline-1,3-dione (1.0 g, 4.60 mmol). The reaction was heated at 70° C. and for 8 h. The reaction was allowed to cool to room temperature and maintained overnight. The reaction was diluted with EtOAc, washed with ice cold water, dried (Na2SO4), filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (Analogix, SF40-115 g, 20-100% EtOAc in hexanes). The pure fractions were combined and evaporated to dryness and triturated with 10% EtOAc in hexanes, filtered and evaporated to dryness to give 2-(2,6-dimethyl-4-oxo-4H-pyran-3-yl)methyl)isoindoline-1,3-dione (290 mg, 1.024 mmol, 22.24% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 7.91-7.74 (m, 4 H), 6.06 (s, 1 H), 4.54 (s, 2 H), 2.43 (s, 3 H), 2.22 (s, 3 H). MS(ES) [M+H]+ 284.0.

후처리

  1. temperatureto cool to room temperature
  2. temperaturemaintained overnight
  3. washwashed with ice cold water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica gel chromatography (Analogix
  8. customevaporated to dryness
  9. customtriturated with 10% EtOAc in hexanes
  10. filtrationfiltered
  11. customevaporated to dryness

출처 및 근거

ORD 기록
ord-86a81e7ba5e140e19d116f530394757f
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382234B2

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