Water → Methyl 7-phthalimidohept-5-ynoate

HRID 358618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358618
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21].O>CN(C)C=O>[C:1]1(=[O:11])[N:5]([CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Komponenten

5

Edukt 3

HCID 962WaterHCID 11287432Methyl 7-bromohept-5-ynoateHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 20066955Methyl 7-phthalimidohept-5-ynoateAusbeute 44,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture or potassium phthalimide (2.31 g) and methyl 7-bromohept-5-ynoate (3.0 g) in dimethylformamide (35 ml) was heated at 110° C. for 4.5 hours. The cooled solution was poured into water (75 ml) and the pH of the solution was adjusted to 6. The resulting solution was extracted with ether (4×200 ml) and the combined ether extracts were dried over magnesium sulphate, the solvent was removed and the residue was chromatographed on silica gel eluted with chloroform to give the title compound (1.56 g) m.p. 62°-63° C.

Aufarbeitung

  1. extractionThe resulting solution was extracted with ether (4×200 ml)
  2. dry with materialthe combined ether extracts were dried over magnesium sulphate
  3. customthe solvent was removed
  4. customthe residue was chromatographed on silica gel
  5. washeluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-c47cfd8ad65b48ce8bb0d9166b2d69ef
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997847

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