Hexane → 2-(4-hydroxybutyl)-1H-Isoindole-1,3(2H)-dione

HRID 726712

反応式

HRID 726712 の反応式
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.C(N1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29])(OCC)=O.CCCCCC>O1CCCC1.C(OCC)(=O)C>[OH:6][CH2:5][CH2:4][CH2:3][CH2:2][N:1]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29]

参加物

7

反応物 4

HCID 8058HexaneHCID 8471TriethylamineHCID 258684-Amino-1-butanolHCID 31187N-Carbethoxyphthalimide

生成物 1

HCID 111175282-(4-hydroxybutyl)-1H-Isoindole-1,3(2H)-dione収率 65.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

A solution of 4-amino-1-butanol (5.616 g; 63 mmol) and triethylamine (12.3 ml; 88.2 mmol) in 130 ml tetrahydrofuran was treated with N-carbethoxyphthalimide (13.82 g; 63 mmol). The mixture was refluxed for 18 hours. TLC showed the formation of product (1:1 Ethyl acetate:Hexane Rf=0.3). The mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with more ethyl acetate and the organic layers combined, dried (MgSO4), filtered, concentrated and the residue purified by flash chromatography; 200 g silica gel column using 2:3 ethyl acetate:Hexane followed by 1:1 to provide N-(4-hydroxybutyl)phthalimide as a white solid (9.108 g; 65.9% yield). 1H NMR (300 MHz, CDCl3): 1.426 (t, 2H, J=4.93 Hz); 1.597-1.663 (m, 2H); 1.738-1.813 (m, 2H); 3.668-3.768 (m, 4H); 7.715 (m, 2H); 7.838 (m, 2H).

後処理

  1. temperatureThe mixture was refluxed for 18 hours
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with more ethyl acetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue purified by flash chromatography

出典と根拠

ORDレコード
ord-a052719cc3ac4fa19cae3bb6b5e1681b
出典データセット
uspto-grants-1998_01
特許番号
US05710159

関連ノート

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