2-Bromobutane → 2-(sec-butoxy)-1H-isoindole-1,3(2H)-dione

HRID 29158

反応式

HRID 29158 の反応式
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].N12CCCN=C1C[CH2:17][CH2:16][CH2:15][CH2:14]2.BrC(CC)C>CN(C=O)C>[CH:15]([O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7])([CH2:16][CH3:17])[CH3:14]

参加物

5

反応物 3

HCID 65542-BromobutaneHCID 10665N-HydroxyphthalimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

生成物 1

HCID 108227352-(sec-butoxy)-1H-isoindole-1,3(2H)-dione収率 89%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

N-hydroxylphthalimide (18.4 mmol, 3.0 g) was dissolved in anhydrous DMF (20 mL) under nitrogen. To the stirring solution, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (27.6 mmol, 4.13 mL) was injected followed by 2-bromobutane (22.1 mmol, 2.41 mL) and the reaction was warmed to 55° C. After stirring for 18 hour, the reaction was cooled to room temperature and concentrated to a red oil. The reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with saturated aqueous sodium bicarbonate solution, distilled water, brine and dried over magnesium sulfate. The solvent was removed under vacuum providing 3.57 g (89%) of a yellow solid. Rf: 0.8 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73 (2H,m), 4.31 (1H,m), 1.81 (1H,m), 1.64 (1H,m), 1.32 (3H,d), 1.03 (3H,t).

後処理

  1. temperaturethe reaction was cooled to room temperature
  2. concentrationconcentrated to a red oil
  3. customThe reaction was partitioned between ethyl acetate and 1N HCl
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  5. distillationdistilled water, brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-dfeb3f265d5d446e915bd4f1737a0a9c
出典データセット
uspto-grants-2008_09
特許番号
US07419967B2

関連ノート

読み込み中…