Dimethylformamide → 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione

HRID 258647

Reaktionsgleichung

Reaktionsgleichung von HRID 258647
Br[CH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].C(N(CC)CC)C.CN(C)C=O>O>[CH:2]1([O:7][N:8]2[C:9](=[O:18])[C:10]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]3[C:12]2=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8728BromocyclopentaneHCID 10665N-Hydroxyphthalimide

Produkt 1

HCID 102632872-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dioneAusbeute 49,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of bromocyclopentane (14.9 g), N-hydroxyphthalimide (16.3 g), triethylamine (15 ml), and dimethylformamide (30 ml) was stirred for 16 hours, then poured into water (500 ml). The oily mixture was extracted with ethyl acetate, and the combined extracts, after washing (water), drying, and removal of solvent gave a white solid. This solid was recrystallised from ethanol to give N-cyclopentyloxyphthalimide (11.37 g, 49%); m.p. 81.2°-82.5°; νmax. (CHBr3) include 1780, 1720 cm-1 (CO--N--CO), 970 cm-1 (>N--O--<CH); τ values (DMSO-d6) 2.08 (4 Ar-H), 5.12 (cyclopentyl 1-H), 8.18 (4-CH2).

Aufarbeitung

  1. extractionThe oily mixture was extracted with ethyl acetate
  2. washthe combined extracts, after washing (water)
  3. customdrying
  4. customremoval of solvent
  5. customgave a white solid
  6. customThis solid was recrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2f32ca15da8549069242d04abc088488
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04033950

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