N-Hydroxyphthalimide → Ethyl 4-((1,3-dioxoisoindolin-2-yl)oxy)butanoate

HRID 20747

反応式

HRID 20747 の反応式
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7]Br)[CH3:2].[OH:10][N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].CCN(C(C)C)C(C)C.[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7][O:10][N:11]1[C:15](=[O:16])[C:14]2[C:13](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]1=[O:21])[CH3:2]

参加物

6

反応物 4

HCID 10665N-HydroxyphthalimideHCID 25517Ammonium ChlorideHCID 76300Ethyl 4-bromobutyrateHCID 81531Diisopropylethylamine

生成物 1

HCID 10850119Ethyl 4-((1,3-dioxoisoindolin-2-yl)oxy)butanoate収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 4-bromo-n-butyric acid ethyl ester (1.2 g, 6.13 mmol) in dimethylformamide (9 ml) were added N-hydroxyphthalimide (1.5 g, 9.19 mmol) and Hunig base (N,N-diisopropylethylamine, 2.13 mL) at room temperature, and the mixture was stirred at 80° C. over night. The reaction mixture was poured into saturated aqueous ammonium chloride, and the resultant mixture was extracted with ethyl acetate (3×40 ml). The combined organic layers were washed with saturated brine (2×30 ml), dried over Na2SO4, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (100 g, n-hexane/ethyl acetate (2:1)) to give 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-butyric acid ethyl ester (1.47 g, 100%).

後処理

  1. extractionthe resultant mixture was extracted with ethyl acetate (3×40 ml)
  2. washThe combined organic layers were washed with saturated brine (2×30 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography (100 g, n-hexane/ethyl acetate (2:1))

出典と根拠

ORDレコード
ord-3f4a91da137348fab27f70c6fd15f396
出典データセット
uspto-grants-2010_06
特許番号
US07745663B2

関連ノート

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