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N-Hydroxyphthalimide → HCID 19789717、化合物

HRID 1655930
ノート
印刷プレビュー

反応式

HRID 1655930 の反応式
[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][OH:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][O:8][N:29]1[C:30](=[O:39])[C:31]2=[CH:38][CH:37]=[CH:36][CH:35]=[C:32]2[C:33]1=[O:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19789718HCID 19789718、化合物

生成物 1

HCID 19789717HCID 19789717、化合物収率 41%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 3-(methoxymethoxy)propanol (5 g, 41.6 mmol), triphenylphosphine (13.1 g, 50 mmol) and N-hydroxyphthalimide (7.25 g, 44 mmol) in dry tetrahydrofuran (150 ml) was cooled to 0°-5° C. and treated with diethyl azodicarboxylate (8.7 g, 50 mmol) in dry tetrahydrofuran (10 ml) over 1/2 hr. The reaction was then stirred at ambient temperature for 18 hr. The solvent was removed in vacuo and the residue was dissolved in diethyl ether (100 ml) and the mixture cooled to 0°-5° C. for 3 hr. The solid was removed by filtration and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica eluting with hexane:ethyl acetate (70:30) to give the title compound as an oil (4.5 g, 41%). νmax (Film) 2960, 2900, 1800, 1740, 1620, 1480 and 1380 cm-1 ; δH (CDCl3) 2.07 (2H, quintet, J=6.3 Hz, CH2CH2CH2), 3.38 (3H, s, OCH3), 3.77 (2H, t, J=6.3 Hz, CH2OCH2OCH3), 4.33 (2H, t, J=6.3 Hz, CH2ON), 4.66 (2H, s, OCH2O), 7.83 (4H, m, ArH).

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in diethyl ether (100 ml)
  3. temperaturethe mixture cooled to 0°-5° C. for 3 hr
  4. customThe solid was removed by filtration
  5. customthe filtrate was evaporated in vacuo
  6. customThe residue was purified by column chromatography on silica eluting with hexane:ethyl acetate (70:30)

出典と根拠

ORDレコード
ord-d37f754f78ec4e5f945f649a87a8df13
出典データセット
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05252575

反応ノート

読み込み中…

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