Nitrogen → 2-(Cyclopent-3-enyloxy)isoindoline-1,3-dione

HRID 1917493ノート

反応式

HRID 1917493 の反応式
[CH:1]1([OH:6])[CH2:5][CH:4]=[CH:3][CH2:2]1.O[N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.N#N>C(Cl)Cl.O>[CH:1]1([O:6][N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:5][CH:4]=[CH:3][CH2:2]1

参加物

8

反応物 5

HCID 947NitrogenHCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 2814783-Cyclopenten-1-olHCID 5363146Diisopropyl azodicarboxylate

生成物 1

HCID 197740932-(Cyclopent-3-enyloxy)isoindoline-1,3-dione収率 32.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of cyclopent-3-enol (840 mg, 10.0 mmol) in CH2Cl2 (25.0 mL) was added 2-hydroxyisoindoline-1,3-dione (1.96 g, 12.0 mmol) and triphenylphosphine (3.93 g, 15.0 mmol). The resultant mixture was cooled to 0° C. and diisopropylazodicarboxylate (2.95 ml, 15.0 mmol) was slowly added drop wise under N2 atmosphere. The reaction mixture was stirred at ambient temperature for 48 h. To the reaction mixture, H2O (100 mL) was added and extracted with CH2Cl2. The organic layers washed with brine. Dried over anhydrous Na2SO4, filtered and concentrated to provide yellow oil, which was purified by flash chromatography (50% EtOAc-hexane) to yield 2-(cyclopent-3-enyloxy)isoindoline-1,3-dione (740 mg, 32%) as light yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.57-2.87 (m, 4H) 5.12 (t, J=6.19 Hz, 1H) 5.75 (s, 2H) 7.74 (dd, J=5.68, 3.16 Hz, 2H) 7.79-7.87 (m, 2H). MS (ES) [M+H] calculated for C13H12NO3, 230.07; found 230.20.

後処理

  1. extractionextracted with CH2Cl2
  2. washThe organic layers washed with brine
  3. dry with materialDried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide yellow oil, which
  7. customwas purified by flash chromatography (50% EtOAc-hexane)

出典と根拠

ORDレコード
ord-a51bca4f02c1474694d76e8de4b61c16
出典データセット
uspto-grants-2013_12
特許番号
US08618290B2

反応ノート

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