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N-Hydroxyphthalimide → 2-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione

HRID 29159
ノート
印刷プレビュー

反応式

HRID 29159 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].C1CCN2C(=NCCC2)CC1.[CH:24]1([CH2:30]Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CN(C=O)C>[CH:24]1([CH2:30][O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10665N-HydroxyphthalimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137636Cyclohexane, (bromomethyl)-

生成物 1

HCID 140744162-(cyclohexylmethoxy)-1H-isoindole-1,3(2H)-dione

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 (27.6 mmol, 4.13 mL) was injected followed by cyclohexylmethyl bromide (23.0 mmol, 3.21 mL) and the reaction was warmed to 55° C. After stirring for 15 hours, 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, brine and dried over magnesium sulfate. The solvent was removed under vacuum, and the crude product was triturated with hexanes providing 3.05 g (64%) of an off-white colored solid. H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73(2H,m), 3.98 (2H,d), 2.03-1.65 (5H,m), 1.31-1.03 (6H,m).

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, brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under vacuum
  7. customthe crude product was triturated with hexanes providing 3.05 g (64%) of an off-white colored solid

出典と根拠

ORDレコード
ord-1f7bcc198d744108926d6cefdbfb57d4
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07419967B2

反応ノート

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