Cyclohexyl bromide → N-cyclohexyloxyphthalimide

HRID 29168

反応式

HRID 29168 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].[CH2:13]1[CH2:23][CH2:22]N2[C:16](=NCCC2)[CH2:15][CH2:14]1.C1(Br)CCCCC1>CN(C=O)C>[CH:13]1([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])[CH2:14][CH2:15][CH2:16][CH2:22][CH2:23]1

参加物

5

反応物 3

HCID 7960Cyclohexyl bromideHCID 10665N-HydroxyphthalimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

生成物 1

HCID 10467039N-cyclohexyloxyphthalimide

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 (61.3 mmol, 10.0 g) was dissolved in anhydrous DMF (60 mL) under nitrogen. To the stirring solution, DBU (92.0 mmol, 13.75 mL) was injected followed by cyclohexyl bromide (76.6 mmol, 9.43 mL) and the reaction was warmed to 55° C. After stirring for 15 hours, the reaction was warmed to 80° C. for 5 hours, then 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 1N NaOH, brine and dried over magnesium sulfate. The solvent was removed under vacuum and the crude product was triturated with hexanes providing 2.89 g (19%) of a yellow solid. Rf: 0.7 (2:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.80 (2H,m), 7.73(2H,m), 4.21 (1H,m), 2.02-1.98 (2H,m), 1.87-1.82 (2H,m), 1.59-1.53 (4H,m), 1.30-1.24 (2H,m).

後処理

  1. temperaturethe reaction was warmed to 80° C. for 5 hours
  2. temperaturecooled to room temperature
  3. concentrationconcentrated to a red oil
  4. customThe reaction was partitioned between ethyl acetate and 1N HCl
  5. washThe organic layer was washed with 1N NaOH, brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under vacuum
  8. customthe crude product was triturated with hexanes providing 2.89 g (19%) of a yellow solid

出典と根拠

ORDレコード
ord-16dd12d525704f8bb2157302ec748a15
出典データセット
uspto-grants-2008_09
特許番号
US07419967B2

関連ノート

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