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

HRID 726712

반응식

HRID 726712 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a052719cc3ac4fa19cae3bb6b5e1681b
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05710159

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