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1H-Isoindole-1,3(2H)-dione, 2-ethenyl- → {2-[2-(1.3-Dioxo-1,3-dihydro-isoindol-2-yl)-vinyl]-phenyl}-acetic acid

HRID 480360
ノート
印刷プレビュー

反応式

HRID 480360 の反応式
C([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=1)(C)(C)C.[CH:16]([N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])=[CH2:17].C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O>[O:28]=[C:19]1[C:20]2[C:21](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:23])[N:18]1[CH:16]=[CH:17][C:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:7][C:6]([OH:5])=[O:15]
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

8

反応物 4

HCID 770351H-Isoindole-1,3(2H)-dione, 2-ethenyl-HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 53936336Tert-butyl 2-(3-bromophenyl)acetate

生成物 1

HCID 73877575{2-[2-(1.3-Dioxo-1,3-dihydro-isoindol-2-yl)-vinyl]-phenyl}-acetic acid収率 30.5%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 6342Acetonitrile溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

A mixture of 3-bromo-phenyl acetic acid tert-butyl ester (5.64 g, 20.80 mmol), N-vinyl phthalimide (3.60 g, 20.80 mmol), diisopropylethylamine (3.63 g, 28.08 mmol), palladium acetate (107 mg, 0.478 mmol), and tritolylphosphine (475 mg, 1.56 mmol) in acetonitrile (10 mL) was stirred at 90° C. for 20 h. The reaction was cooled to room temperature and ice water (50 mL) was added. EtOAc (50 mL) was added and the organic solution was washed with 5.5% HCl followed by brine. The organic solution was dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (hexanes:EtOAc 9:1 to 4:1) provided the title compound (1.95 g). MS 381 (M+18).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. washthe organic solution was washed with 5.5% HCl
  3. dry with materialThe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (hexanes:EtOAc 9:1 to 4:1)

出典と根拠

ORDレコード
ord-69010a64655a4d408032c62f1cd36cf6
出典データセット
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06649657B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート