3a,4,5,7a-Tetrahydro-1H-isoindole-1,3(2H)-dione → Isoindole

HRID 1477981ノート

反応式

HRID 1477981 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1(=O)[NH:11][C:10](=O)[CH:9]2[CH2:13][CH2:14][CH:15]=[CH:16][CH:8]12>C1COCC1>[CH:10]1[NH:11][CH:7]=[C:8]2[C:9]=1[CH:13]=[CH:14][CH:15]=[CH:16]2

参加物

4

反応物 2

HCID 152779823a,4,5,7a-Tetrahydro-1H-isoindole-1,3(2H)-dioneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 3013853Isoindole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a suspension of LAH (22.80 g, 600 mmol) in THF (600 mL) at 0° C. was added tetrahydrophthalimide (39.45 g, 260.9 mmol) portionwise. After addition, the reaction mixture was stirred at 60° C. for 18 h, then cooled down to 0° C. and quenched carefully with water (25 mL), followed by 15% KOH aqueous solution (25 mL) and another 75 mL of water. The resulting mixture was stirred at rt for 1 h and filtered through a pad of Celite, then washed with DCM (500 mL). The filtrate was concentrated in vacuo to give isoindole as yellow oil, which was used in the next step without purification.

後処理

  1. additionAfter addition
  2. temperaturecooled down to 0° C.
  3. customquenched carefully with water (25 mL)
  4. stirringThe resulting mixture was stirred at rt for 1 h
  5. filtrationfiltered through a pad of Celite
  6. washwashed with DCM (500 mL)
  7. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-bfd6e51c7166434185ceb110919f7c44
出典データセット
uspto-grants-2016_08
特許番号
US09403801B2

反応ノート

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