Methanesulfonic Acid → Phthalimide

HRID 1050458

反応式

HRID 1050458 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 6809Phthalimide収率 22.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-86a81e7ba5e140e19d116f530394757f
出典データセット
uspto-grants-2016_07
特許番号
US09382234B2

関連ノート

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