Triphenylphosphine → 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one

HRID 331264ノート

反応式

HRID 331264 の反応式
[Br:1][C:2]1[C:3](=[O:18])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:8][CH:7]=[C:6]([OH:17])[CH:5]=2.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[O:44]1[CH2:45][CH2:46][N:41]([CH2:40][CH2:39][O:17][C:6]2[CH:5]=[C:4]3[C:9]([C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[C:2]([Br:1])[C:3]3=[O:18])=[CH:8][CH:7]=2)[CH2:42][CH2:43]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 703061762-bromo-6-hydroxy-3-phenyl-1H-inden-1-one

生成物 1

HCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A flask was charged with 2-bromo-6-hydroxy-3-phenyl-1H-inden-1-one (3.0 g, 10.0 mmol) obtained in Step 5, PPh3 (3.93 g, 1.5 eq), 4-(2-hydroxyethyl)morpholine (1.8 mL, 1.5 eq), and THF (33 mL, 0.3M). The resulting mixture was cooled to 0° C. and diisopropyl azodicarboxylate (DIAD, 2.9 mL, 1.5 eq) was added. The reaction mixture was stirred at 0° C. for 30 min and allowed to increase to ambient temperature. After being stirred for 2 h, the solution was concentrated by rotary evaporation under reduced pressure. The residue was dissolved in EtOAc, washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by silica gel column chromatography (EtOAc/hexanes=4:1) to afford the desired product (3.2 g, 78%).

後処理

  1. temperatureto increase to ambient temperature
  2. stirringAfter being stirred for 2 h
  3. concentrationthe solution was concentrated by rotary evaporation under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel column chromatography (EtOAc/hexanes=4:1)

出典と根拠

ORDレコード
ord-3d97c459e88a44089be9b9a97ba78e9a
出典データセット
uspto-grants-2014_11
特許番号
US08877747B2

反応ノート

読み込み中…