Diethyl Ether → Ethyl [4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

HRID 346709ノート

反応式

HRID 346709 の反応式
[CH2:1]([O:3][C:4]1[C:12]2[C:11](=O)[N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=3)[C:9](=[O:26])[C:8]=2[C:7]([O:27][CH2:28][CH3:29])=[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=12)[CH3:2].CCOCC>C(O)(=O)C.[Zn]>[CH2:1]([O:3][C:4]1[C:12]2[CH2:11][N:10]([C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:18][CH:19]=3)[C:9](=[O:26])[C:8]=2[C:7]([O:27][CH2:28][CH3:29])=[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=12)[CH3:2]

参加物

5

反応物 2

HCID 3283Diethyl EtherHCID 20761976Ethyl [4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate

生成物 1

HCID 20761975Ethyl [4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate収率 32.2%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒2 回HCID 176Acetic Acid溶媒

実験手順

Ethyl [4-(4,9-diethoxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetate (33 g, 73 mmol) and zinc (90 g, 1.38 mol) were refluxed in acetic acid for 66 h. An additional quantity of zinc (25 g, 0.38 mol) was added and reflux continued for 18 h. The mixture was filtered hot and the filtrate was evaporated to a yellow solid. The solid was purified by 800 g Biotage column eluting with 20% ethyl acetate/hexane to give a white solid, which was triturated in ether to give a white solid. A further fraction was obtained by crystallisation from the ether residues. A total of 10.2 g, 32% of the title compound was obtained.

後処理

  1. temperaturereflux
  2. filtrationThe mixture was filtered hot
  3. customthe filtrate was evaporated to a yellow solid
  4. customThe solid was purified by 800 g Biotage column
  5. washeluting with 20% ethyl acetate/hexane
  6. customto give a white solid, which
  7. customwas triturated in ether
  8. customto give a white solid

出典と根拠

ORDレコード
ord-4fc5c207ec31412a9cfec0ebd555b79e
出典データセット
uspto-grants-2007_02
特許番号
US07173047B2

反応ノート

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